MXPA99010262A - Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors - Google Patents

Abstract

Aminoalkyl glucosamine phosphate compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosamine ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

Description

AMINOALKILGLUCUCOSAMINE PHOSPHATE COMPOUNDS AND THEIR USE AS ADJUVANTS AND IMMUNO-EFFECTORS BACKGROUND OF THE INVENTION Humoral immunity and cell-mediated immunity are the two main branches of the immune response in mammals. Humoral immunity involves the generation of antibodies to foreign antigens. Antibodies are produced by B lymphocytes. Cell-mediated immunity involves the activation of T lymphocytes, which act on infected cells that carry foreign antigens, or that stimulate other cells to act on infected cells. Both branches of the immune system of mammals are important to fight the disease. Humoral immunity is the main line of defense against bacterial pathogens. In the case of a viral disease, the induction of cytotoxic T lymphocytes (CTL, acronym for its English designation: Cytotoxic T Lymphocytes) seems to be crucial for protective immunity. An effective vaccine stimulates both branches of the immune system to protect against the disease. Vaccines present foreign antigens of disease-provoking agents to a host, so that the host can mount a protective immune response. Frequently vaccine antigens are dead or attenuated forms of the microbes that cause the disease. The presence of non-essential components and antigens in these killed or attenuated vaccines has encouraged considerable efforts to refine the components of the vaccine, including the development of well-defined synthetic antigens, using chemical and recombinant techniques. However, the refining and simplification of microbial vaccines has led to a concomitant loss of potency. Synthetic low molecular weight antigens, while devoid of potentially harmful contaminants, in themselves are not very immunogenic. These observations have led the researchers to add adjuvants to the vaccine compositions to enhance the activity of the refined components of the vaccine. At present, the only adjuvant allowed for human use in the United States is "alum", a group of aluminum salts (eg, aluminum hydroxide, aluminum phosphate, in which vaccine antigens are formulated. In particles, such as "alum", they serve to promote the absorption, processing and presentation of soluble antigens by the macrophage, however, "alum" does not lack side effects and only increases humoral immunity (antibody). An effective adjuvant enhances both a humoral response and a cellular immune response in vaccinated animals Additionally, an adjuvant should enhance the host's natural immune response and not aggravate the host system A well-defined synthetic adjuvant, free of foreign material, It would be stable and easy to manufacture, it would give those qualities, however, the compounds that have been prepared and tested in terms of their capacity Adjuvant (Shimizu and coauthors, 1985, Bulusu and co-authors, 1992, Ikeda and co-authors, 1993, Shimizu and co-authors, 1994, Shimizu and co-authors, 1995, Miyajima and co-authors, 1996), often exhibit toxic properties, are unstable and / or have insubstantial immunostimulatory effects.

The discovery and development of effective adjuvants to improve the efficacy and safety of existing vaccines are essential. The adjuvants impart to the synthetic peptide and carbohydrate antigens sufficient immunogenicity to ensure the success of the synthetic vaccine approach. There continues to be a need for new compounds that have potent immunomodulatory effects.

BRIEF DESCRIPTION OF THE INVENTION The compounds of the present invention are aminoalkyl glucosamine phosphate compounds (AGP, acronym by its English name: Aminoalkyl Glucosamine Phosphate), which are adjuvants and immuno-effectors. An aminoalkyl group (aglycone) is glycosidically linked to a 2-deoxy-2-amino-alpha-D-glucopyranose (glucosamine) to form the basic structure of the claimed molecules. The compounds are phosphorylated at carbon atom 4 or 6 of the glucosamine ring. Additionally, the compounds possess three 3-alkanoyloxyalkanoyl residues. The compounds of the present invention are immunoeffector molecules that increase the production of antibodies in immunized animals, stimulating the production of cytokine and activating the macrophage. In accordance with the present invention, methods for using these compounds as adjuvants and immuno-effectors are described.

DETAILED DESCRIPTION OF THE INVENTION The compounds of the present invention are adjuvant and immunoeffector molecules, which are aminoalkyl glucosamine phosphates (AGP). The compounds comprise a 2-deoxy-2-amino-alpha-D-glucopyranose (glucosamine) in glycosidic bond with an aminoalkyl group (aglycone). The compounds are phosphorylated at carbon atom 4 or 6 of the glucosamine ring, and have three alkanoyloxyalkanoyl residues. The compounds of the present invention are generally described with the formula I: (I) Where X represents an oxygen or sulfur atom; Y represents an oxygen atom or the NH group; "n", "m" and "q" are integers from 0 to 6; R, R2 and R3 represent normal fatty acyl residues having from 7 to 16 carbon atoms; R4 and Rs are hydrogen or methyl; R6 and R are hydrogen, hydroxy, alkoxy, phosphono, phosphono-oxy, sulfo, sulfo-oxy, amino, mercapto, cyano, nitro, formyl or carboxy, and their esters and amides; R8 and Rg are phosphono or hydrogen. The configuration of the 3'-stereogenic centers to which the normal fatty acyl residues are fixed is R or S; but preferably, R. The stereochemistry of the carbon atoms to which R4 or R are fixed may be R or S. It is considered that all stereoisomers, both enantiomers and diastereomers, and mixtures thereof, are within the scope of this invention. invention. The heteroatom X of the compounds of the present invention may be oxygen or sulfur. In a preferred embodiment, X is oxygen. While the stability of the molecules could be affected by a substitution in X, the immunomodulatory activity of the molecules is not expected to change with these substitutions. The number of carbon atoms between the hetero atom X and the nitrogen atom of the aglycone is determined by the variables "n" and "m". The variables "n" and "m" can be integers from 0 to 6. In a preferred embodiment, the total number of carbon atoms between the heteroatom X and the nitrogen atom of the aglycon is about 2 to 6, and very preferable , about 2 to 4. The compounds of the present invention are aminoalkyl glucosamine compounds that are phosphorylated. The compounds may be phosphorylated in the 4 or 6 position (Ra or R9) of the glucosamine ring, and are highly effective if they are phosphorylated in at least one of those positions. In a preferred embodiment, R8 is phosphono and Rg is hydrogen. The compounds of the present invention are hexaacylated; that is, they contain a total of six fatty acid residues. The aminoalkylglucosamine moiety is adhered to the 2-amino and 3-hydroxyl groups of the glucosamine unit, and to the amino group of the aglycon unit, with 3-hydroxyalkanoyl residues. In formula I, these three positions are adhered with 3-hydroxytetradecanoyl moieties. In turn, the 3-hydroxytetradecanoyl residues are substituted with normal fatty acids (R1-R3), provided that there are a total of three 3-n-alkanoyloxytetradecanoyl residues, or six fatty acid groups. The chain length of the normal fatty acids R1-R3 may be from about 7 to about 16 carbon atoms. It is preferred that R1-R3 have from about 9 to about 14 carbon atoms. The chain lengths of these normal fatty acids may be the same or different. Although only normal fatty acids are described, it is expected that the unsaturated fatty acids (ie, the fatty acid portions having double or triple ligatures), substituted in Rr R3 in the compounds of the present invention, produce biologically active molecules . Additionally, slight modifications in the chain length of 3-hydroxyalkanoyl residues are not expected to have dramatic effects on biological activity. The compounds of the present invention are adjuvants and immuno-effectors that increase the generation of antibodies in immunized animals, stimulate the production of cytokines and stimulate the cell-mediated immune response., including a T lymphocyte cytotoxic response. In methods for effecting the immune response of an individual, the compounds of the present invention can be formulated with a pharmaceutically acceptable carrier for injection or ingestion. As used herein, "pharmaceutically acceptable carrier" means a medium that does not interfere with the immunomodulatory activity of the active ingredient, and that is not toxic to the patient to whom it is administered. Pharmaceutically acceptable carriers include oil-in-water or water-in-oil emulsions, aqueous compositions, liposomes, microgranules and microsomes. Formulations of the compounds of the present invention that can be administered parenterally, i.e., intraperitoneally, subcutaneously or intramuscularly, include the following preferred carriers. Examples of preferred carriers for subcutaneous use include a phosphate buffered saline solution (PBS) and 0.01-0.1% triethanolamine in USP water for injection. Suitable carriers for intramuscular injection include 10% USP ethanol, 40% propylene glycol, and the remainder an acceptable isotonic solution, such as 5% dextrose. Examples of preferred carriers for intravenous use include 10% USP ethanol, 40% USP propylene glycol and the USP water moiety for injection. Another acceptable carrier includes 10% USP ethanol and USP water for injection; Another one is 0.01-0.1% triethanolamine in USP water for injection. Pharmaceutically acceptable parenteral solvents are those that provide that a solution or dispersion can be filtered through a 5 micron filter, without separating the active ingredient.

Examples of carriers for administration via mucosal surfaces depend on the particular route. When administered orally, examples are the pharmaceutical grades of mannitol, starch, lactose, magnesium stearate, sodium saccharine, cellulose, magnesium carbonate and the like, with mannitol being preferred. When administered intranasally, examples are polyethylene glycol or glycols, sucrose and / or methylcellulose; and preservatives such as benzalkonium chloride, EDTA may be used, polyethylene glycols being preferred, and when administered by inhalation, suitable carriers are polyethylene glycol or glycols; methylcellulose, dispensing agents and preservatives, with polyethylene glycols being preferred. The compounds of the present invention are administered to individuals in "an effective amount" to effect or increase the immune response of the individual. As used herein, "an effective amount" is that amount which shows a response above and above the vehicle or negative controls. The precise dose of the compounds of the present invention to be administered to a patient will depend on the particular AGP used, the route of administration, the pharmaceutical composition and the patient. For example, when administered subcutaneously to increase an antibody response, the amount of AGP used will be from 1 to about 250 micrograms, preferably around 25 to 50 micrograms, based on administration to a typical adult patient of 70. kg- In the vaccine compositions, the AGPs of the present invention are administered to a warm-blooded animal, including humans, with an antigen. The amount of antigen administered to elicit a desired response can be determined by one of skill in the art, and will vary with the type of antigen administered, with the route of administration and with the immunization schedule. For example, 0.2 μg of tetanus toxoid, administered subcutaneously with the claimed compounds, to a mouse in two immunizations at 21 days apart, elicits a humoral immune response to that antigen.

The compounds of the present invention are synthesized by coupling an N-acyloxyacylated or N-protected aminoalkanol or aminoalkanothiol (the agylic unit), with a suitably protected and / or 3-O-acyloxyacylated glucosamine unit. In a preferred method for preparing the compounds of the present invention (scheme 1), a glycosyl halide N- (2,2,2-trichloroethoxy-carbonyl (Troc)) - protected is coupled (Z = F, Cl, Br ), with an N - [(R) -3-n-alkanoyloxytetradecanoyl] aminoalkane or thiol 2 (possessing R6 and R7 in suitably protected form) by means of a Koenigs-Knorr type reaction, in the presence of mercury salts or of silver, to give the glycoside intermediate 3. Preferably the glucosamine unit 1 has an anomeric chloride atom (Z = Cl), and the coupling catalyst is silver trifluoromethane sulfonate. Intermediate 3 can also be prepared by coupling the aglycone unit 2 with a N-Troc-protected glycosyl acetate (Z = Oac) or a related activated derivative, in the presence of a Lewis acid, as a boron trifluoride etherate. By "activated" it is meant that it has an appropriate displaceable "Z" movable group attached to the anomeric center of the glucosamine unit. The glucosamine unit 1 carries a (R) -3-n-alkanoyloxytetradecanoyl residue in the 3-position, and suitable protecting groups in the 6-hydroxyl and 4-phosphate portions. Typical protecting groups for the phosphate group include, but are not limited to, phenyl, benzyl and o-xylyl. The phosphate group is preferably protected with two phenyl groups. Position 6 may be temporarily protected by blocking groups commonly used in sugar chemistry, such as silyl-, benzyl- or benzyloxymethyl ethers or, alternatively, an alkyl carbonate. The 6-hydroxyl group is preferably protected as a carbonate of 1, 1-dimethyl-2,2,2-trichloroethyl (TCBOC). The trichloroethyl group or protective groups, in the coupled product 3 of Koenigs-Knorr, is / are removed with zinc and the glucosamine nitrogen is selectively acylated with an (R) -3-n-alkanoyloxytetradecanoic acid 4, presence of a suitable coupling reagent, to give the hexaacylated derivative. The remaining protecting groups at 5 are then divided by catalytic hydrogenation in the presence of a palladium or platinum catalyst or by other appropriate means, to give compounds of the formula (I). A suitable starting material for the synthesis of the glycosyl donor 1 is 2- (trimethylsilyl) ethyl-2-amino-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside, from D-glucosamine hydrochloride obtainable in commerce, using published procedures. The conversion of the starting material 2- (trimethylsilyl) -ethyl-glycoside to the glycosyl donor 1 can be achieved by methods known in the art or their modifications, which are described herein. The aglyconic unit 2 can be prepared by N-acyloxyacylation of starting materials obtainable commercially, with an (R) -3-n-alkanoyloxytetradecanoic acid 4, or by N-acyloxyacylation of starting materials which can be obtained by methods described in the chemical literature. Alternatively, the N-acyloxyacyl residue in 2 may be substituted with an appropriate amine protecting group, which is subsequently removed from the coupling reaction, as described in the second preferred embodiment that follows.

In a second preferred method for preparing the compounds of the present invention (scheme 2), the introduction of the (R) -3-n-alkanoyloxytetradeca-noyl and phosphate groups is carried out in the glucosamine and aglycon units, subsequently to the glycosylation reaction (coupling), using N-protecting and O-protecting groups, suitable for the chemical differentiation of the amino and hydroxyl groups present. Preferably the N-Troc-protected glycosyl donor 6 is coupled with an aminoalkanol or thiol 7 N-allyloxycarbonyl (AOC) -protected, in the presence of an appropriate catalyst, to give the aminoalkyl-beta-glycoside 8. It is highly preferred that the glycosyl donor 6 possesses an anomeric acetoxy group (Z = Oac) and that the coupling catalyst is boron trifluoride etherate. Other N-protecting groups for the amino group of the aglycon include, but are not limited to, the commonly used carbamates, obvious to those skilled in the art, such as (t-BOC) of tertbutyl, benzyl (Cbz), 2.2 , 2-trichloro-ethyl (Troc) and 9-fluorenylmethyl (Fmoc). The division of the base-induced acetate groups into the coupling product 8, and the formation of the 4,6-acetonide under normal conditions known in the art, gives the intermediate 9. The 3-O-acylation of 9 with acid (R ) -3-n-alkanoyloxytetradecanoic 4, followed by removal of the N-AOC group from the aglycone, mediated by palladium (O) and N-acylation with the (R) -3-n-alkanoyloxytetradecanoic acid gives the intermediate 10. acetonide hydrolysis and functionalization of positions 4 and 6, as described herein for the preparation of the glycosyl donor 1, gives the intermediate 3 (Y = O), which is then processed as in scheme 1, to give the compounds of the general formula (I). The present invention is further described by way of the following non-limiting examples and test examples, which are given solely for illustrative purposes. It is important to note that the introduction of the (R) -3-n-alkanoyloxytetradecanoyl group and the phosphate group (s) in the glucosamine and aglycon units does not necessarily have to be carried out in the order shown in schemes 1 and 2, or as described in the examples shown below.

SCHEME 1 catalyst Z = halide, OAc, etc., Y = O, NH OR C02H n-CnH23 4R = R1, R2oR3 SCHEME 2 catalyst, 6 Z = halide, OAc, etc., - * • (l) 4 R = Ri, R2 or R3 Examples 1-29 describe methods for forming AGP compounds of the present invention. Test examples 1-7 describe analyzes performed to determine the immunogenicity of these compounds. Table 1 is a list of the chemical composition and the experimental reference numbers for each of the compounds of these examples.

TABLE 1 For all the examples shown: X = Y = O; R4 = R5 = H; m = 0; R8 phosphon; R9 = H. * The stereochemistry of the carbon atom to which R5 is attached in S. ** The stereochemistry of the carbon atom to which R5 is fixed in R. *** Rs is H and R9 is phosphono.

EXAMPLE 1 PREPARATION OF ACIDS (R) -3-n-ALCANOILOXITETRADECANOICOS (1) .- A solution of 19 g (0.074 mol) of methyl 3-oxotetradecanoate in 100 ml of MeOH was degassed, bubbling argon for 15 minutes. 0.187 g (0.111 mmol) of catalyst [(R) -Ru (Binap) CI] 2.Net and 0.5 mL of 2N aqueous HCl were added; and the resulting mixture was hydrogenated at 4.2 kg / cm2 gauge and 40-50 ° C for 18 hours. The reaction was diluted with 250 mL of hexanes, filtered through a short column of silica gel and concentrated. The crude product was dissolved in 200 ml of tetrahydrofuran (THF), treated with 83 ml (0.2 mol) of 2.4 N aqueous LiOH and stirred vigorously at room temperature for 4 hours. The resulting suspension was partitioned between 200 ml of ether and 200 ml of 1 N aqueous HCl and the layers were separated. The aqueous layer was extracted with 100 ml of ether and the combined ether extracts were dried over sodium sulfate and concentrated. The crude hydroxy acid was dissolved in 250 ml of hot acetonitrile, treated with 17 ml (0.085 mol) dicyclohexylamine (DCHA) and stirred at 60 ° C for one hour. The product which crystallized on cooling was collected and recrystallized from 650 ml of acetonitrile to give 28.6 g (91%) of dicyclohexylammonium (R) -3-hydroxytetradecanoate as a colorless solid.; p.f. 94-95 ° C. NMR with 1H (CDCI3) delta 0.88 (around t, 3H, J around 6.5 Hz), 1.05-1.58 (m, 24 H), 1.65 (m, 2H), 1.80 (m, 4H), 2.01 (broad d) , 4H), 2.18 (dd, 1 H, J = 15.7, 9.4 Hz), 2.36 (dd, 1 H, J = 15.7, 2.6 Hz), 2.94 (m, 2H), 3.84 (m, 1 H). (2) .- To a mixture of 50 g (0.117 mol) of the compound prepared in (1) above and 39 g (0.14 mol) of 2,4'-dibromoacetophenone in 2.3 liters of EtOAc, 19.6 ml (0.14 mol) was added. ) of triethylamine and the resulting solution was stirred for 18 hours at room temperature. The voluminous precipitate that formed was collected and triturated with 3 x 400 ml of warm EtOAc. The combined triturates and the filtrate were washed with 1 M aqueous HCl, with saturated aqueous NaCl and dried over sodium sulfate. The volatiles were removed under reduced pressure and the obtained crude product was crystallized from EtOAc-hexanes to give 47.2 g (91%) of p-bromophenacyl ester of (R) -3-hydroxytetradecanoic acid, as a colorless solid; p.f. 109-109.5 ° C. NMR with 1H (CDCI3) delta 0.88 (around t, 3H, J around 6.5 Hz), 1.15-1.70 (m, 20 H), 2.56 (dd, 1 H, J = 15.1, 9.1 Hz), 2.69 (dd) , 1 H, J = 15.1, 2.9 Hz), 3.27 (broad s, 1 H), 4.12 (m, 1 H), 5.31 (d, 1 H, J = 16.5 Hz), 5.42 (d, 1 H, J = 16.5 Hz), 7.65 (d, 2H, J = 8.5 Hz), 7.78 (d, 2H, J = 8.5 Hz). (3) .- A solution of 4.6 g (10.4 mmol) of the compound prepared in (2) above was treated in 50 ml of methylene chloride containing 0.12 g (1.0 mmol) of 4-dimethylaminopyridine and 5 ml (52 mmol). of pyridine, at room temperature, with 3.1 ml (11.4 mmol) of myristoyl chloride. After stirring for 5 hours at room temperature, 0.5 ml of MeOH was added and the reaction mixture was concentrated. The residue was partitioned between 150 ml of ether and 50 ml of cold 10% aqueous HCl, and the layers were separated. The ether layer was dried over sodium sulfate and concentrated, and the residue obtained was purified on a short pad of silica gel with 5% EtOAc-hexanes. The diester was dissolved in 42 ml of AcOH and treated with three equal portions of zinc powder (about 6 g, 90 mmol) at 60 ° C for a period of one hour. After a further hour at 60 ° C, the cold reaction mixture was sonically treated for 5 minutes, filtered through Celite® and concentrated. The residue was purified by flash chromatography on silica gel with 10% EtOAc-hexanes to give 4.17 g (82%) of (R) -3-tetradeca-noyloxytetradecanoic acid as a colorless solid; p.f. 28-29 ° C. NMR with 1H (CDCl 3) delta 0.88 (around t, 6H), 1.15-1.40 (m, 38 H), 1.50-1.70 (m, 4H), 2.28 (t, 2H, J = 7.4 Hz), 2.56 (dd, 1 H, J = 15.9, 5.8 Hz), 2.63 (dd, 1H, J = 15.9, 7.1 Hz), 5.21 (m, 1H). (4) .- In the same manner as described in example 1- (3), 2.5 g (5.68 mmol) of the compound prepared in example 1- (2) were acylated with 1.45 ml (6.25 mmol) of lauroyl, in the presence of 0.57 ml (7.0 mmol) of pyridine in 60 ml of methylene chloride and then deprotected with 9.3 g (142 mmol) of zinc in 40 ml of AcOH to produce (R) -3-dodecanoyloxytetradecanoic acid, as a colorless oil. 1 H NMR (CDCl 3) delta 0.90 (t, 6 H, J = 6.5 Hz), 1.0-1.75 (m, 46 H), 2.30 (m, 2 H), 2.62 (m, 2 H), 5.22 (m, 1 H) . (5) .- 2.5 g (5.68 mmol) of a solution of the compound prepared in example 1- (2) was treated with 1.16 g (6.25 mmol) of undecanoic acid and 2.08 g (7.0 mmol) of EDC-Mel in 60 g. ml of methylene chloride and then deprotected as described in Example 1 - (3) with 9.3 g (142 mmol) of zinc in 40 ml of AcOH, to give (R) -3-undecanoyloxytetradecanoic acid, as a colorless oil . NMR with 1H (CDCl 3) delta 0.89 (t, 6H, J = 6.7 Hz), 1.0-1.75 (m, 44H), 2.29 (m, 2H), 2.61 (m, 2H), 5.22 (m, 1 H). (6) .- In the same manner as described in example 1- (3), 4.4 g (10 mmol) of the compound prepared in example 1- (2) was acylated with 2.3 ml (11 mmol) of decanoyl, in the presence of 1.2 ml (15.0 mmol) of pyridine in 100 ml of methylene chloride and then deprotected with 16.4 g (250 mmol) of zinc in 60 ml of AcOH to give (R) -3-decanoyloxytetradecanoic acid, as a colorless oil. NMR with 1H (CDCI3) delta 0.89 (t, 6H, J = 6.8 Hz), 1.0-1.75 (m, 34H), 2.29 (t, 2H, J = 7.4 Hz), 2.61 (t, 2H, J = 4.2 Hz ), 5.22 (m, 1 H). (7) .- In the same manner as described in example 1- (3), 2.5 g (5.68 mmol) of the compound prepared in example 1- (2), with 1.13 ml (6.25 mmol) of chloride were acylated. of nonanoyl, in the presence of 0.57 ml (7.0 mmol) of pyridine in 60 ml of methylene chloride, and then deprotected with 9.3 g (142 mmol) of zinc in 40 ml of AcOH, to give acid (R) -3- nonanoyloxytetradecanoic, as a colorless oil. NMR with 1H (CDCI3) delta 0.89 (t, 6H, J = 6.9 Hz), 1.0-1.75 (m, 32H), 2.29 (t, 2H, J = 7.5 Hz), 2.61 (m, 2H), 5.22 (m, 1H). (8) .- In the same manner as described in example 1- (3), 2.5 g (5.68 mmol) of the compound prepared in example 1- (2) were acylated with 1.07 ml (6.25 mmol) of octanoyl chloride. in the presence of 0.57 ml (7.0 mmol) of pyridine in 60 ml of methylene chloride and then deprotected with 9.3 g (142 mmol) of zinc in 40 ml of AcOH, to give (R) -3-octanoyloxytetradecanoic acid, as a colorless oil. NMR with 1H (CDCl 3) delta 0.92 (t, 6H, J = 6.9 Hz), 1.0-1.75 (m, H), 2.32 (t, 2H, J = 7.4 Hz), 2.63 (t, 2H, J = 4.4 Hz), 5.23 (m, 1 H). (9) .- In the same manner as described in example 1- (3), 2.5 g (5.68 mmol) of the compound prepared in example 1- (2) were acylated with 0.97 ml (6.25 mmol) of heptanoyl chloride in the presence of 0.57 ml (7.0 mmol) of pyridine in 60 ml of methylene chloride and then deprotected with 9.3 g (142 mmol) of zinc in 40 ml of AcOH, to give (R) -3-octanoyloxytetradecanoic acid, as a colorless oil. NMR with 1H (CDCI3) delta 0.89 (t, 6H, J = 6.8 Hz), 1.0-1.75 (m, 28 H), 2.29 (t, 2H, J = 7.4 Hz), 2.61 (d, 2H, J = 5.8 Hz), 5.22 (m, 1 H).

EXAMPLE 2 (B1) PREPARATION OF THE TRIETHYLMONIUM SALT OF 3-HYDROXY- (S) -2-r (R) -3-TETRADECANOILOXITETRADECANOILAMINO1PROPIL-2-DESOXI-4-O-PHOSPHONO-2-r (R -3-TETRADECANOILOXITETRADECANOILAMIN01 -3-O -. (R.-3-TETRADECANOILOXlTETRADECANOILI-ß-D-GLUCOPIRANOSIDA (COMPOSED fi), Ri = R? = Ra = n-C ^ H27CO, X = Y = 0, n = m = q = 0: R4 = R, R7 = RQ = H: Rfi = OH: p = 1. R »= PO, H > . (1) .- To a solution of 6.46 g (20.2 mmol) of 2- (trimethylsilyl) ethyl-2-amino-2-deoxy-4,6-0-isopropyl-den-β-D-glucopyranoside in 300 ml of chloroform was added 300 ml of 1 N aqueous sodium bicarbonate and 8.5 g (40 mmol) of 2,2,2-trichloroethyl chloroformate. The resulting mixture was stirred vigorously for three hours at room temperature. The organic layer was separated, dried over sodium sulfate and concentrated to give a colorless syrup. Flash chromatography on silica gel (gradient elution, 30-40% EtOAc-hexanes) yielded 9.6 g (96%) of 2- (trimethylsilyl) ethyl-2-deoxy-4,6-0-isopropylidene-2-. (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as a colorless solid, e.g. F. 69-70 ° C. NMR with 1H (CDCl 3) delta 0.0 (s, 9H), 0.94 (m, 2H), 1.44 and 1.52 (2s, 6H), 2.94 (broad s, 1 H), 3.23-3.37 (m, 2H), 3.48-3.62 (m, 2H), 3.79 (t, 1 H, J = 10.5 Hz), 3.88-4.08 ( m, 3H), 4.65 (d, 1 H, J = 8.3 Hz), 4.74 (m, 2H), 5.39 (d, 1 H, J = 7.4 Hz). (2) .- A solution of 7.5 g (15.2 mmol) of the compound prepared in (1) above, 7.58 g (16.7 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid and 0.25 g (1.7 mmol) of 4- pyrrolidinopyridine in 95 ml of methylene chloride, with 4.94 g (16.7 mmol) of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide methoiodide (EDC) and stirred for 16 hours at room temperature. The reaction mixture was filtered through a short pad of Celite®, concentrated and the resulting residue was heated at 60 ° C in 100 ml of 90% aqueous AcOH for one hour. The mixture was concentrated and the residual AcOH and water were removed to form azeotrope with 2 x 150 ml of toluene. The crude diol was purified by flash chromatography on silica gel (gradient elution, 30-40% EtOAc-hexanes) to give 11.8 g (83%) of 2- (trimethylsilyl) ethyl-2-deoxy-3-0- [(R) -3-tetra-decanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbonyl-amino) -β-D-glucopyranoside, as an amorphous solid. 1 H NMR (CDCl 3) delta 0.0 (s, 9H), 0.9 (m, 8H); 1.1-1.7 (m, 42H), 2.30 (t, 2H, J = 7.4 Hz), 2.52 (m, 2H), 3.36-3.72 (m, 4H), 3.78-4.03 (m, 3H), 4.57 (d, 1 H, J = 8.3 Hz), 4.65 (d, 1 H, J = 11 Hz), 4.77 (d, 1 H, J = 11 Hz), 5.0-5.15 (m, 2H), 5.20 (d, 1H, J = 7.4 Hz). (3) .- A solution of 10.9 g (12 mmol) of the compound prepared in (2) above and 2 ml (25 mmol) of pyridine in 125 ml of methylene chloride at 0 ° C was treated dropwise for 15 minutes. , with a solution of 3.17 g (13.2 mmol) of 2,2,2-trichloro-1,1-dimethylethyl in 25 ml of methylene chloride.

The reaction mixture was allowed to slowly warm to room temperature for 3.5 hours. Sequentially 0.89 g (6.0 mmol) of 4-pyrrolidinopyridine, 10.5 ml (60 mmol) of N, N-diisopropylethylamine and 3.7 ml (18 mmol) of diphenyl chlorophosphate were added, and the resulting mixture was stirred for 5 hours at room temperature. ambient. The reaction mixture was diluted with 500 ml of methylene chloride, washed with 2 x 250 ml of 7.5% aqueous HCl, at room temperature, with 250 ml of water, with 250 ml of saturated aqueous sodium bicarbonate, dried over sodium sulfate and then concentrated. The residue obtained was purified by flash chromatography on silica gel, eluting with 12.5% EtOAc-hexanes to give 15.1 g (95%) of 2- (trimethylsilyl) ethyl-2-deoxy-4-0-diphenylphosphon-3-0. - [(R) -3-tetradecanoyloxytetradeca-noyl] -6-0- (2,2,2-tri-chloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxy-carbonylamino) -β -D-glucopyranoside, as a viscous oil. NMR with 1H (CDCl 3) delta 0.0 (s, 9H), 0.8-1.0 (m, 8H), 1.1-1.65 (m, 42 H), 1.83 and 1.90 (2s, 6H), 2.15-2.45 (m, 4H) , 3.34 (c, 1 H, J = about 8 Hz), 3.37 (m, 1 H), 3.81 (m, 1H), 3.94 (m, 1 H), 4.27 (dd, 1 H, J = 12, 5 Hz), 4.34 (d, 1H, J = 12 Hz), 4.58 (d, 1 H, J = 12 Hz), 4.66 (c, 1 H, J = about 9 Hz), 4.86 (d, 1H, J = 12 Hz), 5.03 (d, 1H, J = 7.9 Hz), 5.21 (m, 1H), 5.54-5.70 (m, 2H), 7.2-7.8 (m, 10H). (4) .- A solution of 1.87 g (1.41 mmol) of the compound prepared in (3) above in 3 ml of methylene chloride at 0 ° C was treated dropwise for 10 minutes with 6 ml of trifluoroacetic acid (TFA). ); then it was stirred for 4 hours at 0 ° C. The reaction mixture was concentrated and the residual TFA was removed to form azeotrope with 2 x 5 ml of toluene. A solution of 2.2 ml (28.2 mmol) of lactol and dimethylformamide in 14 ml of methylene chloride at 0 ° C was treated dropwise with 2.1 ml (4.2 mmol) of 2.0 M oxalyl bromide in methylene chloride for 15 minutes. minutes, and the resulting suspension was stirred at 0 ° C for 24 hours. The reaction mixture was partitioned between 25 ml of cold saturated aqueous sodium bicarbonate and 50 ml of ether and the layers were separated. The ether layer was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated to give 1.85 g (about 100%) of 2-deoxy-4-0-diphenylphosphono-3-0 - [( R) -3-tetradecanoyloxytetradeca-noyl] -6-0- (2,2,2-trichloro-1,1-dimethyl-ethoxycarbonyl-2- (2,2,2-trichloroethoxycarbonylamino) -alpha-D-glucopyranosyl), like a colorless glass. (5) .- A solution of 0.46 g (2.33 mmol) of (R) -2-amino-3-benzyloxy-1-propanol and 1.29 g (2.83 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid in 20% was treated. ml of methylene chloride, with 0.78 g (2.79 mmol) of EDC-Mel and stirred for 16 hours at room temperature. The reaction mixture was filtered through a short pad of Celite® and concentrated. Flash chromatography on silica gel with 45% EtOAc-hexanes afforded 1.1 g (69%) of 3-benzyloxy- (R) -2 - [(R) -3-tetradecanoyloxytetradecanoylamino-propanol as a colorless solid.; p.f. 42-44.5 ° C. 1 H NMR (CDCl 3) delta 0.88 (t, H, J = about 6.5 Hz), 1.0-1.7 (m, 42 H); 2.50 (t, 2H, J = 7.5 Hz), 2.46 (m, 2H), 3.56 (broad s, 1 H), 3.5-3.75 (m, 3H), 3.78 (dd, 1 H, J = 11.4Hz), 4.08 (m, 1 H), 4.51 (s, 2H), 5.17 (m, 1 H), 6.36 (d, 1 H, J = 7.8 Hz), 7.2-7.4 (m, 5H). (6) .- To a solution of 1.00 g (0.776 mmol) of the compound prepared in (4) above and 0.35 g (0.57 mmol) of the compound prepared in (5) above) in 4.5 ml of dichloroethane, 1.25 g of powdered molecular sieves of 4 Á and 2.7 g (20 mmol) of calcium sulfate. After stirring for 10 minutes at room temperature, the mixture was treated with 1.0 g (4.0 mmol) of mercuric cyanide and then heated under reflux for 12 hours, protected from light. The reaction mixture was diluted with 25 ml of methylene chloride and filtered through a pad of Celite®. The filtrate was washed with 25 ml of 1 N aqueous Kl, dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel with EtOAc-hexanes-MeOH (80: 20: 0-70: 30: 1), gradient elution) to give 0.66 g (63%) of 3-benzyloxy- (S) -2 - [(R) -3-tetradecanoyloxytetra-decanoylamino] propyl-2-deoxy-4-0-phosphono-3-0 - [(R) -tetradeca-noyloxytetradecanoyl] -6-0- (2,2,2 -trichloro-1, 1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glycopyranoside as an amorphous solid. NMR with 1H (CDCI3) delta 0.88 (t, 12 H, J = about 6.5 Hz), 1.0-1.65 (m, 84 H), 1.79 and 1.86 (2s, 6H), 2.1-2.5 (m, 8H), 3.35-3.55 (m, 3H), 3.65-3.8 (m, 3H), 4.1-4.75 (m, 9H), 5.05-5.3 (m, 2H); 5.3-5.5 (m, 2H), 6.04 (d, 1 H, J = 8.4 Hz), 7.05-7.45 (m, 15 H). (7) .- A stirred solution of 0.60 g (0.328 mmol) of the compound prepared in (6) above was treated in 9 ml of AcOH at 55 ° C, with 1.1 g (16 mmol) of zinc powder in three equal portions. , for an hour. The cooled reaction mixture was sonically treated, filtered through a pad of Celite® and concentrated. The resulting residue was partitioned between 60 ml of methylene chloride and 35 ml of cold 1N aqueous HCl, and the layers were separated. The organic layer was washed with 5% aqueous sodium bicarbonate, dried over sodium sulfate and concentrated. A mixture of the obtained residue and 0.18 g (0.39 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid in 3.5 ml of methylene chloride was stirred with 0.1 g of molecular sieves sprayed at 4 A for 30 minutes at room temperature, and then it was treated with 0.12 g (0.49 mmol) of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ). The resulting mixture was stirred for six hours at room temperature, filtered through Celite® and then concentrated. Chromatography on silica gel (gradient elution, 0.5-1% MeOH-chloroform) yielded 0.31 g (50%) of 3-benzyloxy- (S) -2 - [(R) -3-tetradecanoyloxytetradecanoylamino] propyl-2 -deoxy-4-0-diphenylphosphono-2 - [(R) -3-tetradecanoyloxytetradecanoyl-amino] -3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -β-D-glucopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.88 (t, 18H, J = 6.5 Hz), 1.0-1.8 (m, 126 H), 2.1-2.5 (m, 12H), 3.35-3.75 (m, 6H), 3.80 (m, 2H), 4.23 (m, 1H), 4.46 (d, 1H, J = 12 Hz), 4.51 (d, 1H, J = 12 Hz), 4.65 (c, 1H, J = about 9.5 Hz), 4.82 (d, 1H, J = 8.1 Hz), 5.05 -5.25 (m, 3H), 5.47 (t, 1 H, J = around 9. 5 Hz), 6.16 (d, 1 H, J = 8.1 Hz), 6.31 (d, 1 H, J = 8.4 Hz), 7.1-7.4 (m, 15 H). (8) .- A solution of 0.26 g (0.138 mmol) of the compound prepared in (7) above was hydrogenated in 25 ml of THF, in the presence of 50 mg of 5% palladium on carbon, at room temperature and atmospheric pressure. , for 16 hours. After removing the catalyst by filtration, 3 ml of AcOH and 0.14 g of platinum oxide were added and the hydrogenation was continued at room temperature and 5.27 kg / cm 2 gauge for 24 hours. The resulting opalescent reaction mixture was diluted with 20 ml of 2: 1 chloroform-MeOH and sonically treated for a short time, to give a clear solution. The catalyst was collected, washed with 2 x 5 ml of 2: 1 chloroform-MeOH and the combined filtrate and washings were concentrated. The residue was dissolved in 10 ml of 1% aqueous triethylamine and sonically treated for 5 minutes at 35 ° C and the resulting solution was lyophilized. Flash chromatography on silica gel with chloroform-methanol-water-triethylamine (gradient elution 94: 6: 0.5: 0.5-88: 12: 1.0: 1.0) yielded 0.20 g (84%) of product as a colorless powder. A 0.166 g portion of the chromatography product was dissolved in 33 ml of 2: 1 chloroform-MeOH and washed with 14 ml of cold 0.1 N aqueous HCl. The lower organic layer was filtered and concentrated, and the obtained free acid was lyophilized in 15 ml of 1% aqueous, pyrogen-free triethylamine to give 0.160 g of the triethylammonium salt of 3-hydroxy- (S) - 2 - [(R) -tetradecane-ioxytetradecanoylamino] propyl-2-deoxy-4-0-phosphono-2 - [(R) -3-tetradecanoyl-xitetradecanoylamino] -3-0 - [(R) -3-tetradecane- iloxytetradecanoyl] -β-D-glucopyranoside, as a colorless solid; p.f. 178-180 ° C (decomposition). IR (film) 3293, 3103, 2959, 2924, 2855, 1732, 1654, 1640, 1553, 1467, 1377, 1259, 1175, 1106, 1086, 1050, 803, 720 cm "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18 H, J = 7 Hz), 1.0-1.7 (m, 135 H), 2.15-2.75 (m, 12H), 3.02 (c, 6H, J = 7 Hz), 3.35-4.1 (m , 7H), .22 (c, 1 H, J = about 9.5 Hz), 4.77 (d, 1 H, J = 8 Hz), 5.05-5.35 (m, H), 6.58 (d, 1 H, J = 6 Hz), 6.73 (d, 1 H, J = 7.5 Hz, NH). NMR with 13 C (CDCl 3) delta 173.5, 173.2, 170.7, 170.5, 170.0, 100. 7, 75.9, 72.7, 71.2, 71.0, 70.8, 70.6, 67.9, 61.7, 60.5, 55.0, 50.4, 45.6, 1.4, 39.5, 34.5, 34.4, 32.0, 31.8, 30.3, 29.8, 29.4, 29.3, 5.3, 25.1, 22.7, 14.2, 8.6. Analysis calculated for C? GH192N3O? ßP: C, 64.84; H, 11.10; N, 2.29; P, 1.69; Found: C, 64.69; H, 11.24; N, 1.93; P, 1.44.

EXAMPLE 3 (B2) PREPARATION OF THE TRIETHYLMONIUM SALT OF 3-HYDROXY- (R) -2-r (R.- 3-TETRADECANOILOXITETRAPECANOILAMINO1PROPIL-2-PESOXI-4-O-PHOSPHONO-2-G, R) -3- TETRADECANOILOX ?? TRADECANOILAMINO1-3-O-rR-3-TETRADECANOILOXn? TRADECANOILI-ß-P-GLUCOPIRANOSIDA.

(COMPOUND (I) Ri - R2 = R3 = NC ... Hr.CO: X = Y = O: n = m = q = 0: R4 = Rs = R7 = Rg = H: RB = OH; p = 1, RB = PO, H ?. (1) .- A solution of 0.63 g (1.02 mmol) of the compound prepared in Example 2- (5), with 0.4 ml (5 mmol) of pyridine, 4-dimethylaminopyridine (catalyst) and 0.307 g (1.23 g) was treated sequentially. mmol) of 2,2,2-trichloro-1,1-dimethylethyl chloroformate, and stirred for 16 hours at room temperature. The reaction mixture was diluted with 25 ml of methylene chloride, washed with 25 ml of saturated aqueous sodium bicarbonate and dried over sodium sulfate. Removal of the volatiles, under vacuum, gave a residue which was dissolved in 10 ml of 9: 1 THF: AcOH and hydrogenated in the presence of 150 mg of 5% palladium on carbon, at room temperature and atmospheric pressure, for 24 hours. After removing the catalyst by filtration and concentrating the filtrate, the residue was purified by flash chromatography on silica gel, with 35% EtOAc-hexanes, to give 0.536 g (72%) of 3- (2,2,2-trichloro-1,1-dimethylethoxycarbonyloxy) - (S) -2 - [(R) -3- tetradecanoiloxitetrade-canoilaminojpropanol, as an amorphous solid. NMR with 1H (CDCI3) delta 0.88 (t, 6H, J = 6.5 Hz), 1.1-1.7 (m, 42H), 1.94 (s, 6H), 2.30 (t, 2H, J = 7.5 Hz), 2.47 (d, 2H, J = 6 Hz), 3.50 (broad s, 1 H), 3.72 (m, 2H), 4.15-4.35 (m, 3H), 5.15 (m, 1 H), 6.18 (d, 1 H) , J = 7.2 Hz). (2) .- In the same manner as described in Example 2- (6), 0.310 g (0.426 mmol) of the compound prepared in (1) above and 0.961 g (0.745 mmol) of the compound prepared in the example were coupled. 2- (4), in the presence of 0.43 g (1.7 mmol) of mercuric cyanide to give 0.644 g (78%) of 3- (2,2,2-trichloro-1,1-dimethylethyloxycarbonyloxy) - (S) -2 - [(R) -3-tetradecanoyloxytetradecanoylamino] propyl-2-deoxy-4-O-phosphono-3-0 - [(R) -tetradecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1) , 1-dimethyl-ethoxycarbonyl) -2- (2,2,2-trichloro-ethoxycarbonylamino) -β-D-glycopyranoside, as an amorphous solid. NMR with 1H (CDCI3) delta 0.88 (t, 12H, J = 6.5 Hz), 1.0-1.7 (m, 84 H), 1.81 and 1.89 (2s, 6H), 1.93 (s, 6H), 2.15-2.55 (m , 8H), 3.45-3.7 (m, 2H), 3.80 (broad d, 1 H, J = 9 Hz), 3.9-4.45 (m, 6H), 4.6-4.8 (m, 3H), 4.87 (d, 1 H, J = 8.1 Hz), 5.0-5.25 (m, 2H), 5.48 (t, 1 H, J = about 9.5 Hz), 6.1-6.3 (m, 2H). (3) In the same manner as described in Example 2- (7), 0.602 g (0.310 mmol) of the compound prepared in (2) above was deprotected with 1.5 g (23 mmol) of zinc and acylated with 0.17 g (0.37 mmol) of (R) -3-tetradecanoyloxy-tetradecanoic acid in the presence of 0.115 g (0.467 mmol) of EEDQ, to give 0.365 g (66%) of 3-hydroxy- (R) -2 - [( R) -3-tetradecanoyl-oxytetradecanoyl-amino] propyl-2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -3-0 - [(R) -3-tetra-decanoyloxytetradecanoyl] -β-D-glucopyranoside, as an amorphous solid. NMR with 1H (CDCI3) delta 0.88 (t, 18H, J = 6.5 Hz), 1.0-1.7 (m, 126 H), 2.15-2.55 (m, 12H), 3.18 (broad s, 1 H), 3.45-3.8 (m, 8H), 3.85-4.05 (m, 2H), 4.69 (c, 1 H, J = 9.5 Hz), 5.05-5.25 (m, 3H), 5.42 (t, 1 H, J = about 9.5 Hz ), 6.42 (d, 1 H, J = 7.8 Hz), 6.59 (d, 1 H, J = 7.2 Hz), 7.1-7.4 (m, 10H). (4) .- In the same manner as described in Example 2- (8), 0.355 g (0.196 mmol) of the compound prepared in (3) above was hydrogenated, in the presence of 175 mg of platinum oxide, to give 0.265 g (77%) of the triethylammonium salt of 3-hydroxy- (R) -2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -propyl-2-deoxy-4-0-phosphono-2 - [(R) -3-tetradecanoyloxytetradeca-noylamino] -3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -β-D-glucopyranoside, as a colorless solid; p. F. 159-160 ° C. IR (film) 3291, 2956, 2922, 2853, 1738, 1732, 1716, 1650, 1643, 1556, 1468, 1171, 1109, 1083, 1051 cnrf1. 1H-NMR (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.5 Hz), 1.0-1.7 (m, 135 H), 2.15-2.75 (m, 12H), 3.06 (c, 6H, J = 7 Hz) ), 3.25-3.45 (m, 2H), 3.5-4.05 (m, 12H), 4.19 (c, 1 H, J = 9.5 Hz), 4.48 (d, 1 H, J = 8.4 Hz), 5.04-5.26 ( m, 4H); 7.18 (d, 1 H, J = 7.8 Hz), 7.27 (d, 1 H, J = 8.7 Hz). NMR with 13 C (CDCl 3) delta 173.5, 173.4, 170.7, 170.6, 170.1 101. 0, 76.0, 72.6, 71.4, 71.0, 70.8, 70.6, 68.6, 68.7, 61.8, 60.5, 55.3, 50.5, 45.6, 41.5, 41.5, 41.5, 41.5, 34.5, 34.2, 34.4, 34.3, 32.0, 29.8, 29.4, 25.4, 25.4, 25.1, 22.7, 14.1, 8.6. Analysis calculated for C99H? 92N3? 18P.H20: C, 67.50; H, 11.10; N, 2.39; P, 1.76. Found: C, 67.40; H, 11.22; N, 2.34; P, 2.11.

EXAMPLE 4 (B3) PREPARATION OF THE TRIETHYLMONIUM SALT OF 3-HYDROXY- (S) -2-r (R) -3-DODECANOILOXITETRADECANOILAMIN01PROPIL-2-DESOXI-4-Q-PHOSPHONO-2-r (R -3-DODECANOILOXITETRADECANOILAMINQ1 -3-Or (R.- 3-DOPECA-NOILOXITETRADECANOIL1-ß-D-GLUCOPIRANOSIDA (COMPOUND (i), Ri = R2 = R ^ = n-CnH ^ CO: X = Y = O: n = m = q = 0: R? _ = R, = R7 = Ro = H: Rfi = OH: p = 1: R «= PO, H, i. (1) .- A solution of 20 g (92.8 mmol) of D-glucosamine hydrochloride in 250 ml of H20, with 250 ml of saturated aqueous sodium bicarbonate and 14.05 ml (102 mmol) of chloroformate of 2.2 was treated. , 2-trichloroethyl and stirred vigorously for 18 hours. The white solid that formed was collected in a fritted funnel and dried under vacuum for 24 hours. It cooled to 0 ° C a solution of the solid in 100 ml of pyridine and treated with 100 ml of acetic anhydride, by means of an addition funnel. The solution was stirred for 18 hours at room temperature, poured into 1 liter of water and extracted with 3 x 500 ml of chloroform. The solvent was removed in vacuo to give 45 g (quantitative) of N- (2,2,2-trichloroethoxycarbonyl-amino) -1,4,4,6-tetra-0-acetyl-2-deoxy-alpha-D-glucopyranoside, which was used without further purification . NMR with 1H (CDCl 3) delta 2.06 (s, 6H), 2.12 (s, 3H), 2.22 (s, 3H), 4. 03 (m, 1 H), 4.07 (d, 1 H, J = 12.4 Hz), 4.22 (dt, 1 H, J = 9.9, 3.6 Hz), 4.30 (dd, 1 HOUR; J = 12.4, 4.0 Hz), 4.64 (d, 1 H, J = 9.6 Hz), 5.28 (dt, 1 H, J = 10.2, 9.9 Hz), 6. 25 (d, 1 H, J = 3.6 Hz). (2) .- A solution of 5 g (27.6 mmol) of (R) -2-amino-3-benzyloxy-1-propanol in 250 ml of methylene chloride was treated with 3.2 ml (30 mmol) of chloroformate. allyl and 250 ml saturated aqueous sodium bicarbonate for 18 hours. The organic layer was separated and concentrated in vacuo. Purification by chromatography eluting with 30% EtOAc / hexanes afforded 6.9 g (94%) of (R) -2- (allyloxycarbonylamino) -3-benzyloxy-1-propanol, as an amorphous solid. NMR with 1H (CDCI3) delta 2.56 (s broad 1 H), 3.69 (m, 3H), 3.88 (m, 2H), 4.54 (s, 2H), 4.58 (d, 2H, J = 5.6 Hz), 5.23 ( dd, 1 H, J = 10.4, 1.1 Hz), 5.33 (dd, 1H, J = 17.1, 1.1 Hz), 5.42 (m, 1 H), 5.93 (m, 1 H), 7.35 (m, 5H). (3) .- A solution of 8.9 g (17 mmol) and 3.6 g (10 mmol), respectively, of the compound prepared in (1) and (2) above, was treated with 4.3 ml (34 mmol) of trifluoride etherate. of boron, at room temperature, for 16 hours. The reaction mixture was quenched with 100 ml of saturated aqueous sodium bicarbonate and extracted with 3 x 100 ml EtOAc. The combined EtOAc extracts were dried over sodium sulfate, and concentrated. The residue obtained was chromatographed with 20% EtOAc / hexanes to give 6.03 g (83%) of 3-benzyloxy- (S) -2- (allyloxycarbonylamino) propyl-2-deoxy-3,4,6-tri-0 -acetyl-2- (2, 2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as an amorphous solid. 1 H NMR (CDCl 3) delta 2.02 (s, 3 H), 2.03 (s, 3 H), 2.08 (s, 3 H), 3.45 (m, 1 H), 3.54 (m, 1 H), 3.64 (m, 1 H) ); 3.76 (d, 1 H, J = 7.2 Hz), 3.91 (m, 2H), 4.12 (d, 1 H, J = 12.2 Hz), 4.26 (dd, 1 H, J = 12.4, 4.7 Hz), 4.37 ( d, 1 H, J = 8.2 Hz), 4.43 (d, 1 H, J = 12.1 Hz), 4.55 (m, 2H), 4.68 (mn, 2H), 4.87 (d, 1 H, J = 8.0 Hz) , 5.07 (m, 2H); 5.21 (d, 1 H, J = 9.7 Hz), 5.29 (d, 1 H, J = 17.3 Hz), 5.91 (m, 1 H), 7.36 (m, 5H). (4) .- A solution of 6.0 g (8.3 mmol) of the compound prepared in (3) above, in 83 ml of methanol, was treated with 8.3 ml of ammonium hydroxide, at room temperature, for 2 hours. The solvent was removed under vacuum and replaced with 50 ml of 2,2-dimethoxypropane and 100 mg of camphorsulfonic acid was added. The reaction was stirred for 18 hours, neutralized with 1 g of solid sodium bicarbonate, filtered and concentrated in vacuo. Purification by chromatography with 50% EtOAc / hexanes yielded 4.58 g (86%) of 3-benzyloxy- (S) -2- (allyloxycarbonylamino) propyl-2-deoxy-4,6-0-isopropylidene-2- (2 , 2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside. 1 H NMR (CDCl 3) delta 1.46 (s, 3 H), 1.53 (s, 3 H), 2.94 (m, 1 H), 3.25 (m, 1 H), 3.55 (m, 4 H), 3.83 (m, 3 H), 3.93 (m, 3H); 4.52 (m, 5H), 4.68 (d, 1 H, J = 12.1 Hz), 4.77 (d, 1 H, J = 12.1 Hz), 5.07 (m, 1 H), 5.26 (m, 2H); 5.92 (m, 1 H); 7.37 (m, 5H). (5) .- A solution of 1.0 g (1.56 mmol) of the compound prepared in (4) above was treated in 20 ml of methylene chloride, with 730 mg (1.71 mmol) of (R) -3-dodecanoyloxy-tetradecanoic acid , in the presence of 560 mg (1.87 mmol) of EDCMel and 50 mg of 4-pyrrolidinopyridine. The reaction was stirred at room temperature for 18 hours and filtered through a plug of 6 x 8 cm silica gel, using 20% EtOAc / hexanes as eluent to give 1.33 g (82%) of 3-benzyloxy - (S) -2- (allyloxycarbonylamino) propyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-dodecanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbonylamino) - β-D-glucopyranoside, as an amorphous solid.

NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.8 Hz), 1.1 -1.6 (m, 38 H), 1.37 (s, 3H), 1.46 (s, 3H), 2.28 (t, 2H, J = 7.4 Hz), 2.49 (dd, 1 H, J = 15.1, 6.0 Hz), 2.61 (dd, 1 H, J = 15.1, 6.6 Hz), 3.25-4.0 (m, 9H, 4.38 (m, 2H), 4.54 (m, 2H), 4.65 (m, 2H), 4.97 (m, 2H), 5.25 (m, 5H), 5.88 (m, 1 H), 7.34 (m, 5H). (6) .- To a solution of 1.31 g (1.25 mmol) of the compound prepared in (5) above in 20 ml of THF, 1.0 ml, 0.88 mmol) of dimethyl malonate was added and the solution was degassed in a stream of Argon, for 30 minutes. 200 mg of tetracis (triphenylphosphine) -palladium (0) was added and the reaction was stirred at room temperature for 2 hours, and then concentrated in vacuo. The residue obtained was chromatographed on silica gel, eluting with 5-10% EtOAc / chloroform. The obtained free amine was acylated with 560 mg (1.38 mmol) of (R) -3-dodecanoyloxytetradecanoic acid in the presence of 370 mg (1.5 mmol) of EEDQ in 15 ml of methylene chloride. After stirring at room temperature for 18 hours the solvent was removed under vacuum and the resulting oil was chromatographed on silica gel, eluting with 20% EtOAc / hexanes, to give 1.02 g (63%) of 3-benzyloxy- ( S) -2 - [(R) -3-dodecanoyloxytetradecanoylamino] propyl-2-deoxy-4,6-0-isopro-pylidene-3-0 - [(R) -3-dodecanoyloxytetradecanoyl] -2- (2.2 , 2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as a colorless amorphous solid.

NMR with H (CDCI3) delta 0.88 (t, 12H, J = 6.9 Hz), 1.1-1.7 (m, 78 H), 1.38 (s, 3H), 1.46 (s, 3H), 2.26 (m, 4H), 2.49 (dd, 1 H, J = 15.1, 6.0 Hz), 2.61 (dd, 1 H, J = 15.1, 6.6 Hz), 3.25-4.0 (m, 9H), 5.01 (m, 2H), 6.02 (d, 1 H, J = 8.4 Hz), 7.34 (m, 5H). (7) .- 1.0 g (0.78 mmol) of the compound prepared in (6) above was treated with 20 ml of 90% aqueous AcOH for one hour at 60 ° C. The solution was concentrated in vacuo and the residual AcOH and water were removed to form azeotropes with 10 ml of toluene. The residue was dissolved in methylene chloride, cooled to 0 ° C and treated with 0.076 ml (0.94 mmol) of pyridine and a solution of 205 mg (0.86 mmol) of 2,2,2-trichloro-chloroformate, 1-dimethylethyl in 5 ml of methylene chloride. The reaction mixture was then allowed to warm and stirred at room temperature for 18 hours. The resulting light yellow solution was treated with 0.24 ml (1.17 mmol) of diphenyl chlorophosphate, 0.22 ml (1.56 mmol) of triethylamine and 50 mg of catalytic 4-pyrrolidinopyridine, and then stirred for another 24 hours at room temperature. The reaction mixture was diluted with 100 ml of ether and washed with 50 ml of 10% aqueous HCl. The organic phase was separated, dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel using 10% EtOAc / hexanes yielded 1.13 g (85%) of 3-benzyloxy- (S) -2 - [(R) -3-dodecanoyloxytetradecanoylamino] propyl-2-deoxy-4-0 -diphenyl-phosphono-3-0 - [(R) -3-dodecanoyloxytetradecanoyl] 6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonyl) -mino) -β-D-glucopyranoside, as an amorphous, colorless solid. 1 H NMR (CDCl 3) delta 0.87 (t, 12 H, J = 6.9 Hz), 1.1-1.6 (m, 78 H), 1.78 (s, 3 H), 1.86 (s, 3 H); 2.01 (m, 1 H); 2.18 (m, 3H), 2.40 (m, 2H), 2.67 (m, 1 H), 2.88 (d, 1 H, J = 6.6 Hz), 2.97 (d, 1 H, J = 6.9 Hz), 3.41 ( m, 2H), 3.72 (m, 1 H), 3.82 (m, 1 H), 4.24 (m, 1 H), 4.42 (d, 1 H, J = 11.8 Hz), 4.64 (m, 3H), 5.16 (m, 1 H), 5.39 (m, 2H); 5.75 (d, 1 H, J = 4.3 Hz), 6.05 (d, 1 H, J = 8.4 Hz), 7.23 (m, 15H). (8) .- In the same manner as described in Example 2- (7), 1.1 g (0.65 mmol) of the compound prepared in (7) above was deprotected with 2.1 g (32 mmol of zinc) and acylated with 330 mg (0.78 mmol) of (R) -3-dodecanoyloxytetra-decanoic acid in the presence of 230 mg (0.94 mmol) of EEDQ, to give 399 mg (37%) of 3-benzyloxy- (S) -2- [ (R) -3-dodecanoyloxytetradeca-aminolamino] propyl-2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-dodeca-noyloxytetradecanoylamino] -3-0 - [(R) -3-dodecanoyltetradecanoyl] - β-D-glucopyranoside, as a colorless amorphous solid. (9) .- In the same way that was written in the example 2- (8), 399 mg (0.24 mmol) of the compound prepared in (8) above was hydrogenated, in the presence of 150 mg of palladium hydroxide on carbon in 10 ml of EtOH and 300 mg of platinum oxide in EtOH / AcOH (10: 1) , to give 65 mg (16%) of the triethylammonium salt of 3-hydroxy- (S) -2 - [(R) -3-dodecanoyloxytetradeca-noylamino] propyl-2-deoxy-4-0-phosphono-2- [(R) -3-dodecanoiloxite-tradecanoylamino] -3-0 - [(R) -3-dodecanoyloxytetradecanoyl] -β-D-glucopyranoside, as a white powder; p.f. 181-184 ° C (decomposition).

IR (film) 3306, 2956, 2922, 2852, 1732, 1644, 1549, 1467, 1377, 1164, 1106, 1051, 721 cm. "1 NMR with 1H (CDCI3-CD3OD)) delta 0.88 (t, 18H, J = 6.7 Hz), 1.1-1.7 (m, 123H), 2.2-2.7 (m, 12H), 3.06 (c, 6H, J = 7.1 Hz), 3.3-4.0 (m, 13 H), 4.23 (m, 1 H), 4.44 (d, 1 H, J = 7.7 Hz), 5.0-5.3 (m, 4H). NMR with 13C (CDCI3) delta 173.9, 173.5, 173.3, 170.8, 170.5, 170.1, 101.0, 75.5, 73.0, 71.1, 70.9, 70.6, 67.9, 61.6, 60.7, 54.4, 50.4, 45.8, 41.6, 39.6, 34.6, 31.9, 29.7, 29.4, 29.4, 29.3, 25.4, 25.1, 22.7, 14.2, 8.6 Analysis calculated for C93Hi8oN3O? 8P.H2 ?: C, 66.59; H, 10.94; N, 2.50; P, 1.85; Found: C, 66.79; H, 10.65; N, 2.36; P, 1.70; EXAMPLE 5 (B4) PREPARATION OF THE TRIETHYLMONIUM SALT OF 3-HIPROXY- (S.-2 -. (R.- 3-UNPECANOILOXITETRAPECANOILAMINO1PROPIL-2-PESOXI-4-O-PHOSPHONO-2 -. (R.-3-UNPECANOILOX ?? TRAPECANOILAMINO1- 3-QG (R.- 3-UNPECANOILOXITETRAPECANOILI-ß-d-GLUCOPIRANQSIPA (COMPOUND (0, R. = R2 = R3 = N-CmH2.CQ, X = Y = O: n = m = q = 0: R = R, = R7 = Rg = H: Rfi = OH: p = 1 : R »= PQ, H, i (1) .- In the same manner as described in Example 4- (5), 1.0 g (1.56 mmol) of the compound prepared in Example 4- (4) was acylated with 705 mg (1.71 mmol) of acid (R) -3-undecanoyloxytetradecanoic, in the presence of 560 mg (1.87 mmol) of EDC-Mel and 50 mg of 4-pyrrolidinopyridine in 20 ml of methylene chloride, to give 1.23 g (77%) of 3-benzyloxy- ( S) -2- (allyloxycarbonylamino) propyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-undecanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbonyl) - β-D-glucopyranoside, as an amorphous solid. 1 H NMR (CDCl 3) delta 0.88 (t, 6 H, = 6.9 Hz), 1.1 -1.6 (m, 36H), 1.37 (s, 3H), 1.46 (s, 3H), 2.28 (m, 2H); 2.52 (dd, 1 H, J = 15.1, 6.0 Hz), 2. 61 (dd, 1 H, = 15.5, 6.8 Hz), 3.25 (m, 1 H), 3.35-4.0 (m 9H), 4.31 (m, 2H), 4.54 (m, 2H); 4.64 (m, 2H), 5.02 (m, 2H), 5.18 (m, 2H), 5.25 (m, 1 H), 5.86 (m, 1 H), 7. 34 (m, 5H). (2) .- In the same manner as described in example 4- (6), 1.21 g (1.17 mmol) of the compound prepared in (1) above was deprotected in 20 ml of THF, in the presence of 1.0 ml (0.88). mmol) of dimethyl malonate and 200 mg of tetracis-triphenylphosphine) palladium (O); and then acylated with 540 mg (1.30 mmol) of (R) -3-undecanoyloxytetradecanoic acid, in the presence of 370 mg (1.5 mmol) of EEDQ, to give 921 mg (61%) of 3-benzyloxy- (S) - 2 - [(R) -3-undecanoyloxytetradecanoylamino] propyl-2-deoxy-5,6-0-isopropylidene-3-0 - [(R) -3-undecanoyloxytetradeca-noyl] -2- (2,2,2- trichloroethoxycarbonylamino) -β-D-glucopyranoside, as an amorphous, colorless solid.

NMR with 1H (CDCl 3) delta 0.88 (t, 12H, J = 6.6 Hz), 1.1-1.7 (m, 72H), 1.38 (s, 3H), 1.46 (s, 3H), 2.26 (m, 3H), 2.38 (m, 5H), 2.49 (dd, 1 H, J = 15.2.6.0 Hz), 2.61 (dd, 1 H, J = 15.0, 6.5 Hz), 3.25-4.0 (m, 9H), 4.30 (m, 2H ); 4.59 (m, 3H), 6.03 (d, 1 H, J = 8.2 Hz, 7.34 (m, 5H). (3) .- In the same way as described in Example 4- (7), 910 was unprotected. g (0.71 mmol) of the compound prepared in (2) above, in 20 ml of 90% aqueous AcOH and treated with 0.071 ml (0.88 mmol) of pyridine and 195 mg (0.80 mmol) of 2.2, 2 chloroformate. -trichloro-1,1-dimethylethyl in methylene chloride, followed by 0.23 ml (1.10 mmol) of diphenyl chlorophosphate, 0.20 ml (1.46 mmol) of triethylamine and 50 mg of catalytic 4-pyrrolidinopyridine, to give 1.10 g (89%) ) of 3-benzyloxy- (S) -2 - [(R) -3-undecanoyloxytetradecanoylamino] propyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-undecanoyloxytetradeca-noyl] -6 -0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as a colorless amorphous solid. RMN with 1H (CDCl 3) delta 0.87 (t, 12H, J = 6.7 Hz), 1.1-1.6 (m, 72H), 1.78 (s, 3H), 1.86 (s, 3H), 2.01 (m, 1 H), 2.18 (m, 3H), 2.40 (m, 2H), 2.67 (m, 1 H), 2.88 (d, 1 H, J = 6.7 Hz), 2 .97 (d, 1 H, J = 6.9 Hz), 3.41 (m, 2H), 3.72 (m, 1 H), 3.82 (m, 1 H), 4.24 (m, 1 H), 4.42 (d, 1 H, J = 11.8 Hz), 4.64 (m, 3H); 5.16 (m, 1 H), 5.39 (m, 2H), 5.75 (d, 1 H, J = 4.6 Hz), 6.05 (d, 1 H, J = 8.4 Hz), 7.22 (m, 15H). (4) .- In the same way as described in example 2- (7), 1.0 g (0.59 mmol) of the compound prepared in (3) above was deprotected with 2.0 g (30 mmol) of zinc and acylated with 292 mg (0.71 mmol) of (R) -3-undecanoyloxytetradecanoic acid in the presence of 210 mg (0.85 mmol) of EEDQ, to give 388 mg (40%) of 3-benzyloxy- (S) -2 - [(R) -3-undecanoyloxytetradecanoylamino] propyl-2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-undecanoyloxytetradecanoylamino] -3-0 - [(R) -3-unde-canoyltetradecanoyl] -β-D-glucopyranoside, as an amorphous, colorless solid. (5) .- In the same manner as described in Example 2- (8), 388 mg (0.24 mmol) of the compound prepared in (4) above was hydrogenated in the presence of 150 mg of palladium hydroxide on carbon, in 10 ml of EtOH and 300 mg of platinum oxide in EtOH / AcOH (10: 1), to give 65 mg (17%) of the triethylammonium salt of 3-hydroxy- (S) -2 - [(R) -3-undecanoyloxy-tetradecanoylamino] propyl-2-deoxy-4-0-phosphono-2 - [(R) -3-undeca-noyloxytetradecanoylamino] -3-0 - [(R) -3-undecanoyloxytetradeca-noyl] -β -D-glucopyranoside, as a white powder; p.f. 183-184 ° C. IR (film) 3306, 2956, 2922, 2852, 1732, 1644, 1550, 1467, 1377, 1164, 1106, 1052, 721 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.8 Hz), 1. 1-1.7 (m, 117H), 2.2-2.7 (m, 12H), 3.07 (c, 6H, J = 7.1 Hz), 3.3-3.9 (m, 13H), 4.23 (m, 1H), 4.45 (d, 1 H, J = 8.2 Hz), 5.0-5.3 (m, 4H). NMR with 13C (CDCI3) delta 173.8, 173.5, 173.3, 170.8, 170.5, 170.1, 101.0, 75.5, 73.1, 71.5, 71.3, 70.9, 70.6, 67.8, 61.6, 60.7, 54.4, 50.5, 45.8, 41.5, 41.4, 39.5 , 34.6, 34.4, 32.0, 31.2, 29.8, 29.7, 29.4, 28.6, 26.1, 25.4, 25.1, 22.7, 14.1, 8.6. Analysis calculated for C9oH- | 4N30 8P.H20: C, 66.10; H, 10.85; N, 2.57; P, 1.89; Found: C, 66.34; H, 10.69; N, 2.32; P, 1.99.

EXAMPLE 6 (B5) PREPARATION PE SALT PE TRIETILAMONIQ PE 3-HYPROXY- (S.-2-r (R.- 3-PECANOYLOXITETRAPECANOILAMINO1PROPIL-2-PESOXI-4-O-PHOSPHONO-2-r (R.-3- PECANOYLOXITETRAPECANOILAMINO1-3-Q -. (R.-3- PECANOYLOXITETRAPECANOILI-ß-d-GLUCOPIRANQSIPA (COMPOUND (I), Ri = R2 = R3 = n-C9H? GCO, X = Y = Q; n = m = q = 0: R4 = Rs = R7 = Rg = H: Rfi = OH; p = 1; Ra = POaH?) (1) .- In the same manner as described in Example 4- (5), 2.0 g (3.12 mmol) of the compound prepared in Example 4- (4) was added with 1.36 g (3.42 mmol) of acid ( R) -3-decanoyloxytetradecanoic, in the presence of 1.12 g (3.74 mmol) of EDCMel and 100 mg of 4-pyrrolidinopyridine in 40 ml of methylene chloride, to give 2.49 g (79%) of 3-benzyloxy- (S) - 2- (Allyloxycarbonylamino) propyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-decanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbo-nylamino) -β-D -glucopyranoside, as an amorphous solid. NMR with 1H (CDCI3) delta 0.88 (t, 6H, J = 6.7 Hz), 1.1-1.6 (m, 34H), 1.36 (s, 3H), 1.46 (s, 3H), 2.27 (t, 2H; J = 6.9 Hz), 2.48 (dd, 1 H, J = 15.1, 6.0 Hz), 2.60 (dd, 1 H, J = 15.1, 6.7 Hz), 3.25 (m, 1 H), 3.35-4.0 (m, 9H) , 4.23 (m, 1 H), 4.42 (m, 1 H); 4.62 (m, 4H), 4.95 (m, 2H), 5.17 (m, 3H), 5.88 (m, 1 H), 7.36 (m, 5H). (2) .- In the same manner as described in example 4- (6), 2.47 g (2.42 mmol) of the compound prepared in (1) above was deprotected in 40 ml of THF, in the presence of 2.0 ml (1.75 mmol). ) of dimethyl malonate and 400 mg of tetracis (triphenylphosphine) palladium (0), and then acylated with 1.06 g (2.66 mmol) of (R) -3-decanoyloxytetradecanoic acid, in the presence of 740 mg (3 mmol) of EEDQ , to give 1.86 g (60%) of 3-benzyloxy- (S) -2 - [(R) -3-decanoyloxytetradecanoylamino] propyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R ) -3-decanoyloxytetradecane-yl] -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as a colorless amorphous solid. NMR with 1H (CDCl 3) delta 0.87 (t, 12H, J = 6.7 Hz), 1.1-1.7 (m, 68 H), 1.37 (s, 3H), 1.46 (s, 3H), 2.32 (m, 4H), 2.50 (dd, 1 H, J = 15.1, 6.0 Hz), 2.62 (dd, 1 H, J = 15.1 , 6.8 Hz), 3.29 (m, 2H), 3.44 (m, 1 H), 3.55 (m, 1 H), 3.74 (m, 3H), 3.93 (m, 1 H), 4.18 (m, 1 H) , 4.34 (m, 1H), 4.57 (d, 1 H, J = 11.8 Hz), 4.65 (m, 2H), 5.01 (m, 2H), 6.04 (d, 1 H, J = 8.3 Hz), 7.36 ( m, 5H). (3) .- In the same manner as described in example 4- (7), 900 mg (0.72 mmol) of the compound prepared in (2) above was deprotected in 40 ml of 90% aqueous AcOH and then treated with 0.071 ml (0.88 mmol) of pyridine and 195 mg (0.809 mmol) of 2,2,2-trichloro-1,1-dimethylethyl chloroformate in methylene chloride, followed by 0.23 ml (1.10 mmol) of diphenyl chlorophosphate , 0.20 ml (1.46 mmol) of triethylamine and 50 mg of catalytic 4-pyrrolidinopyridine, to give 1.05 g (86%) of 3-benzyloxy- (S) -2 - [(R) -3-decanoyloxytetradecanoylamino] propyl-2- Deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-decanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2 , 2- trichloroethoxycarbonylamino) -β-D-glucopyranoside, as an amorphous, colorless solid. 1 H NMR (CDCl 3) delta 0.87 (t, 12 H, J = 6.3 Hz), 1.1-1.6 (m, 68 Hz), 1.78 (s, 3 H), 1.86 (s, 3 H), 2.01 (m, 1 H) , 2.18 (m, 3H), 2.40 (m, 2H), 2.67 (m, 1 H), 2.88 (d, 1 H, J = 6.5 Hz), 2.97 (d, 1 H, J = 6.9 Hz), 3.41 (m, 2H), 3.72 (m, 1 H), 3.82 (m, 1 H, 4.24 (m, 1 H), 4.42 (d, 1 H, J = 11.8 Hz), 4.64 (m, 3H), 5.16 (m, 1 H), 5.39 (m, 2H), 5.75 (d, 1 H, J = 4.3 Hz), 6.05 (d, 1H, J = 8.4 Hz), 7.22 (m, 15H). (4) .- In the same manner as described in Example 2- (7), 1.0 g (0.60 mmol) of the compound prepared in (3) above was deprotected with 2.0 g (30 mmol) of zinc and acylated with 285 mg (0.72 mmol) of (R) -3-decanoyloxytetrade-canoic acid, in the presence of 210 mg (0.86 mmol) of EEDQ, to give 332 mg (34%) of 3-benzyloxy- (s) -2- [ (R) -3-decanoyloxytetradeca-noylamino] propyl-2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-decanoyloxytetradecanoylamino] -3-0 - [(R) -3-decanoyltetradecanoyl] - β-D-glucopyranoside, as a colorless amorphous solid. (5) .- In the same manner as described in Example 2- (8), 332 mg (0.20 mmol) of the compound prepared in (4) above was hydrogenated, in the presence of 150 mg of palladium hydroxide on carbon in 10%. ml of EtOH and 300 mg of platinum oxide in EtOH / AcOH (10: 1) to give 173 mg (55%) of the triethylammonium salt of 3-hydroxy- (S) -2 - [(R) -3- decanoyloxy-tetradecanoylamino] propyl-2-deoxy-4-0-phosphono-2 - [(R) -3-decanoyloxytetradecanoylamino] -3-0 - [(R) -3-decanoi? oxytetradecanoyl] -β-D- beta glucopyranoside, as a white powder; p.f. 179-181 ° C. IR (film) 3295, 2956, 2923, 2853, 1732, 1650, 1555, 1467, 1377, 1320, 1169, 1134, 1104, 1051, 979, 801, 721 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.9 Hz), 1.1- 1.7 (m, 111H), 2.2-2.7 (m, 12H), 3.07 (c, 6H, J = 6.5 Hz), 3.3-4.3 (m, 14H) , 445 (d, 1 H, J = 8.0 (Hz), 5.0-5.3 (m, 4H), 7.39 (m, 1 H), 7.53 (d, 1 H, J = 9.1 Hz). NMR with 13C (CDCI3) ) delta 173.7, 173.4, 173.2, 170.7, 170.5, 170.1, 101.0, 75.4, 73.1, 71.6, 71.1, 70.8, 70.5, 67.8, 61, 4, 60.8, 54.3, 50.4, 45.8, 41, 3, 39.5, 34.5, 31.9, 29.8, 29.7, 29.4, 25.4, 25.1, 22.7, 14.1, 8.6 Analysis calculated for C8 Hi68N3 ?? 8P.H20: C, 65.58; H, 10.75; N, 2.64; P, 1.94; Found: C, 65.49; H, 10.75; N, 2.64; P, 1.97.

EXAMPLE 7 (B6) PREPARATION PE SALT PE TRIETILAMONIO PE 3-HlPROXI- (S) -2-f (R.- 3-PECANOYLOXITETRAPEANOILAMINO.PROPIL-2-PESOXI-6-O-PHOSPHONO-2-r (R) - 3-PEGANOYLOXITETRAPECANOILAMINOl-3-Or (R) -3- PECANOYLOXI-TETRAPECANOIL.-ß-P-GLUCOPIRANOSIPA (COMPOUND PE Ri = R2 = R, = n-CsHiaCO; X = Y = O; n = msq = 0: FLi - Rs = R7 = R «= H, Rfi = OH: p = 1, Rq = PO, H? (1) .- In the same manner as described in Example 4- (7), 900 mg (0.72 mmol) of the compound prepared in Example 6- (2) was deprotected in 20 mL of 90% aqueous AcOH. The residue was dissolved in 20 ml of methylene chloride, cooled to 0 ° C and treated with 0.14 ml (1.0 mmol) of triethylamine and 0.17 ml (0.8 mmol) of diphenyl chlorophosphate. The mixture was stirred for an additional six hours, and then quenched with 50 ml of 10% HCl. The product was extracted with 3 x 50 ml EtOAc and dried over sodium sulfate. Chromatography on silica gel with 50% EtOAc / hexanes afforded 636 mg (63%) of 3-benzyloxy- (S) -2 - [(R) -3-decanoyloxy-tetradecanoylamino] propyl-2-deoxy-6- 0-diphenylphosphono-3-0 - [(R) -3-decanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbonylamino] -β-D-glucopyranoside, as a colorless amorphous solid.1H-NMR (CDCl3) delta 0.87 (t, 12H, J = 6.0 Hz), 1.1 -1.6 (m, 68 H), 1.79 (s, 3H), 1.86 (s, 3H), 2.01 (m, 1 H), 2.18 (m, 3H) ), 2.40 (m, 2H), 2.67 (m, 1 H), 2.89 (d, 1 H, J = 6.5 Hz), 2.97 (d, 1 H, J = 6.9 Hz), 3.41 (m, 2H), 3.75 (m, 1 H, 3.82 (m, 1 H), 4.24 (m, 1 H), 4.42 (d, 1 H, J = 11.8 Hz), 4.65 (m, 3 H), 5.16 (m, 1 H) , 5.39 (m, 2H), 5.75 (d, 1 H, J = 4.3 Hz), 6.05 (d, 1 H, J = 8.4 Hz), 7.22 (m, 15H). (2) .- In the same manner as described in Example 2- (7), 620 g (0.44 mmol) of the compound prepared in (1) above was deprotected with 722 mg (11 mmol) of zinc and acylated with 190 mg (0.48 mmol) of (R) -3-decanoyloxytetrade-canoic acid in the presence of 170 mg (0.58 mmol) of EEDQ to give 254 mg (36%) of 3-benzyloxy- (S) -2 - [( R) -3-decanoyloxy-tetradecanoylamino] propyl-2-deoxy-6-0-diphenylphospho-2 - [(R) -3-decanoyloxytetradecanoylamino] 3-0 - [(R) -3-decanoyltetradecanoyl] -β-D- glucopyranoside, as an amorphous, colorless solid. (3) .- In the same manner as described in Example 2- (8), 254 mg (0.16 mmol) of the compound prepared in (2) above was hydrogenated in the presence of 150 mg of palladium hydroxide on carbon in EtOH (10 ml) and 300 mg of platinum oxide in EtOH / AcOH (10: 1) to give 34 mg (13%) of the triethylammonium salt of 3-hydroxy- (S) -2 - [(R) - 3-decanoyloxytetradecane-ylamino] propyl-2-deoxy-6-0-phosphono-2 - [(R) -3-decanoyloxytetra-decanoylamino] -3-0 - [(R) -3-decanoyloxydetradecanoyl] -β-D- glucopi -reside, as a white powder; p. F. 169-171 ° C.

IR (film) 3306, 2922, 2853, 1732, 1644, 1548, 1467, 1377, 1316, 1165, 1106, 1053, 856, 722 cm "1.

NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.7 Hz), 1.1-1.7 (m, 111 H), 2.2-2.7 (m, 12H), 3.05 (m, 6H), 3.3-3.95 (m, 12H), 4.11 (m, 1 H), 4.34 (m, 1 H), 4.89 (m, 1 H), 5.0-5.3 (m, 4H). NMR with 13C (CDCI3) delta 173.8, 173.4, 171.1, 170.5, 101.3, 75.3, 74.9, 71.2, 71.0, 70.6, 68.8, 67.3, 65.1, 61.4, 54.4, 50.7, 45.9, 41.5, 41.3, 39.6, 34.6, 32.0 , 29.8, 29.6, 29.4, 25.3, 25.1, 22.7, 14.1, 8.7. Analysis calculated for C87Hi68N3? 18P.H2 ?: C, 65.58; H, 10.75; N, 2.64; P, 1.94; Found: C, 65.60; H, 10.34; N. 2.36; P, 2.01.

EXAMPLE 8 (B7) PREPARATION PE SALT PE TRIETHYLMONIUM PE 3-HYPROXY- (S.-2 -. (R.- 3-NONANOYANOXITETRAPECANOILAMINO1PROPIL-2-PESOXI-4-O-PHOSPHONO-2-r (R.-3- NONANOYLOXlTETRAPECANOILAMINO1-3-O-KR) -3- NONANOILOXI-TETRAPECANOIL.-ß-P-GLUCOPIRANOSIPA (COMPOUND (I), Ri = R? = R * = n-CHH? 7CO; X = Y = O: n = m = q = 0, R¿ = R. = R7 to RQ = H: Rfi = OH, p = 1: RR = PO, H ,. (1) .- In the same manner as described in Example 4 (5), 1.0 g (1.56 mmol) of the compound prepared in Example 4- (4) was acylated with 660 mg (1.71 mmol) of the (R) -3-nonanoyloxytetradecanoic acid, in the presence of 560 mg (1.87 mmol) of EDC.Mel and 50 mg of 4-pyrrolidinopyridine, in 20 ml of methylene chloride, to give 1.31 g ( 83%) of 3-benzyloxy- (S) -2- (allyloxycarbonylamino) propyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-nonanoyloxytetradecanoyl] -2- (2, 2,2-trichloroethoxycarbo-nylamino) -β-D-glucopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.87 (t, 6H, J = 6.8 Hz), 1.1-1.6 (m, 32H), 1.37 (s, 3H), 1.46 (s, 3H), 2.27 (t, 2H, J = 7.4 Hz), 2.50 (dd, 1 H, J = 15.1, 6. 0 Hz), dd, 1 H; J = 15.1, 6.8 Hz), 3.26 (m, 1 H), 3.35-4.0 (m, 9H), 4.32 (d, 1 H, J = 7.8 Hz), 4.41 (d, 1 H, J = 12.0 Hz), 4.51 (m, 4H); 4.95 (m, 2H); 5.18 (m, 2H); 5.29 (d, 1 H, J = 17.2 Hz), 5.88 (m, 1 H); 7.36 (m, 5H). (2) .- In the same manner as described in example 4- (6), 1.29 g (1.28 mmol) of the compound prepared in (1) above was deprotected in 20 ml of THF in the presence of 1.0 ml ( 0.88 mmol) of dimethyl malonate and 200 mg of tetracis (triphenylphosphine) palladium (0), and then acylated with 540 mg (1.41 mmol) of (R) -3-nonanoyloxytetradecanoic acid, in the presence of 370 mg (1.5 mmol) of EEDQ, to give 1.02 g (65%) of 3-benzyloxy- (S) -2 - [(R) -3-nonanoyloxytetradecanoylamino] pro-pil-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-nonanoyloxytetrade-canoyl] -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as a colorless amorphous solid. NMR with 1H (CDCl 3) delta 0.87 (t, 12H, J = 6.1 Hz), 1.1-1.7 (m, 64H), 1.37 (s, 3H), 1.46 (s, 3H), 2.28 (m, 4H), 2.50 (dd, 1 H, J = 15.5, 6.0 Hz), 2.62 (dd, 1 H, J = 14.8, 6.3 Hz), 3.27 (m, 2H), 3.44 (m, 1 H), 3.55 (m, 1 H ), 3.74 (m, 3H), 3.93 (m, 1 H); 4.18 (m, 1 H), 4.34 (m, 2H), 4.57 (d, 1 H, J = 11.8 Hz), 4.65 (m, 2H), 4.97 (t, 1 H, J = 9.6 Hz), 5.06 ( d, 1 H, J = 8.6 Hz), 5.15 (m, 2H), 6.05 (d, 1 H, J = 8.2 Hz), 7.35 (m, 5H). (3) .- In the same manner as described in example 4- (7), 1.0 g (0.81 mmol) of the compound prepared in (2) above was deprotected in 20 ml of 90% aqueous AcOH, treated with 0.080 ml (0.908 mmol) of pyridine and 215 mg (0.89 mmol) of 2,2,2-trichloro-1,1-dimethylethyl chloroformate in methylene chloride, followed by 0.25 ml (1.22 mmol) of diphenyl chlorophosphate, 0.21. ml (1.52 mmol) of triethylamine and 50 mg of catalytic 4-pyrrolidinopyridine, to give 1.17 g (87%) of 3-benzyloxy- (S) -2 - [(R) -3-nonanoyloxytetradecanoylamido] -propyl-2-deoxy -4-0-diphenylphosphono-3-0 - [(R) -3-nonanoyloxytetra-decanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2, 2, 2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as a colorless amorphous solid. 1 H NMR (CDCl 3) delta 0.87 (t, 12 H, J = 6.1 Hz), 1.1-1.6 (m, 64 H), 1.78 (s, 3 H), 1.86 (s, 3 H), 2.01 (m, 1 H) , 2.18 (m, 3H), 2.40 (m, 2H), 2.67 (m, 1 H), 2.88 (d, 1 H, J = 6.5 Hz), 2.97 (d, 1 H, J = 6.9 Hz), 3.41 (m, 2H), 3.72 (m, 1 H), 3.82 (m, 1 H), 4.24 (m, 1 H), 4.42 (d, 1 H, J = 11.8 Hz), 4.64 (m, 3H); 5.16 (m, 1 H), 5.39 (m, 2H), 5.75 (d, 1 H), J = 4.3 Hz), 6.05 (d, 1 H, J = 8.4 Hz), 7.22 (m, 15H). (4) .- In the same manner as described in Example 2- (7), 1.1 g (0.66 mmol) of the compound prepared in (3) above was deprotected with 2.2 g (33 mmol) of zinc and acylated with 305 mg (0.79 mmol) of (R) -3-nonanoyloxytetradecanoic acid, in the presence of 235 mg (0.95 mmol) of EEDQ, to give 373 mg (35%) of 3-benzyloxy- (S) -2 - [(R) -3-nonanoyloxytetradecanoylamino] propyl-2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-nonanoyloxytetradecanoylamino] -3-0 - [(R) -3-nonanoyl-tetradeanoyl] -β-D -glucopyranoside, as a colorless amorphous solid. (5) .- In the same manner as described in example 2- (8), 373 mg (0.23 mmol) of the compound prepared in (4) above was hydrogenated in the presence of 150 mg of palladium hydroxide on carbon in 10 ml of EtOH and 300 mg of platinum oxide in EtOH / AcOH (10: 1), to give 43 mg (12%) of the triethylammonium salt of 3-hydroxy- (S) -2 - [(R) - 3-nonanoyloxy-tetradecanoylamino] propyl-2-deoxy-4-0-phosphono-2 - [(R) -3-nonanoyloxytetradecanoylamino] -3-0 - [(R) -3-nonanoyloxytetradeca-noyl] -β-D- glucopyranoside, as a white powder, p. F. 176-179 ° C. IR (film) 3298, 2956, 2923, 2853, 1733, 1646, 1551, 1467, 1337, 1316, 1254, 1166, 1106, 1053, 722 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.87 (t, 18H, J = 6.7 Hz), 1.1-1.7 (m, 105H), 2.2-2.7 (m, 12H); 3.03 (c, 6H, J = 7.0 Hz), 3.3-4.3 (m, 14H), 4.43 (d, 1H), J = 7.1 Hz), 5.0-5.3 (m, 4H), 7.12 (d, 1 H, H = 7.7 Hz), 7.17 (d, 1 H, J = 8.2 Hz). NMR with 13C (CDCI3) delta 173.9, 173.5, 173.3, 170.8, 170.5, 170.1, 100.9, 75.5, 73.1, 71.4, 71.1, 70.9, 70.6, 67.8, 60.7, 54.3, 50.5, 45.8, 41.6, 41.4, 39.5, 34.6 , 34.4, 32.0, 31.9, 29.8, 29.4, 29.3, 25.4, 25.1, 22.7, 14.1, 8.6. Analysis calculated for C88Hi64N3 ?? 8P: C, 65.81; H, 10.64; N, 2.74; P. 2.02; Found: C, 66.14; H, 10.46; N, 2.58; P, 1.84.

EXAMPLE 9 (B8, PREPARATION PE SALT PE TRIETILAMONIO PE 3-HIPROXl- (S.-2 -. (R.- 3-HEPTANOILOXITETRAPECANOILAMINO1PROPIL-2-PESOXM-O-PHOSPHONO-2-r (R -3-HEPTANOILOXITETRAPECANOILAMINO1-3 -Qr (R) -3- HEPTANOIL-OXITETRAPECANOILl-ß-P-GLUCOPIRANOSIPA (COMPOUND (I), Ri = R? = R3 = n-C? H? ACO; X = Y = O; n = m = q = 0; R_? = Rs = R7 = Rq = H: Rfi = OH: p = 1: RR = PO, H? .. (1) .- In the same manner as described in Example 4- (5), 1.0 g (1.56 mmol) of the compound prepared in Example 4- (4) was acylated with 610 mg (1.71 mmol) of acid ( R) -3-heptanoyloxytetradecanoic, in the presence of 560 mg (1.87 mmol) of EDC-Mel and 50 mg of 4-pyrrolidinopyridine in 20 ml of methylene chloride, to give 1.24 g (82%) of 3-benzyloxy- (S ) -2-allyloxycarbonylamino) propyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-heptanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbo-nylamino) -β- D-glucopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.0 Hz), 1.1-1.6 (m, 28H), 1.38 (s, 3H), 1.47 (s, 3H), 2.29 (t, 2H), J = 7.4 Hz), 2.51 (dd, 1 H, J = . 1, 6.0 Hz); 2.63 (dd, 1 H, J = 15.1, 6.8 Hz), 3.26 (m, 1 H), 3.35-4.0 (m, 9H), 4.32 (d, 1 H, J = 7.3 Hz), 4.41 (d, 1 H, J = 12.0 Hz), 4.61 (m, 4H), 4.95 (m, 2H); . 18 (m, 2H); 5.29 (d, 1 H, J = 17.3 Hz), 5.88 (m, 1 H), 7.36 (m, 5H). (2) .- In the same manner as described in example 4- (6), 1.22 g (1.25 mmol) of the compound prepared in (1) above was deprotected in the presence of 1.0 ml (0.88 mmol) of dimethyl malonate. and 200 mg of tetracis (triphenylphosphine) -palladium (0), and then acylated with 490 mg (1.38 mmol) of (R) -3-heptanoyloxytetradecanoic acid in the presence of 370 mg (1.5 mmol) of EEDQ, to give 925 mg (62%) of 3-benzyloxy- (S) -2 - [(R) -3-heptanoi) oxytetradecanoylamino] propyl-2-deoxy-4,6-0-isopro-piliden-3-0 - [( R) -3-heptanoyloxytetradecanoyl] -2- (2,2,2-trichloro-ethoxycarbonylamino) -β-D-glucopyranoside, as a colorless amorphous solid. NMR with 1H (CDCl 3) delta 0.87 (t, 12H, J = 6.7 Hz), 1.1-1.7 (m, 56H), 1.37 (s, 3H), 1.46 (s, 3H), 2.32 (m, 4H), 2.50 (dd, 1 H, J = 15.1, 6.0 Hz), 2.62 (dd, 1 H, J = 15.1, 6.8 Hz), 3.29 (m, 2H), 3.44 (m, 1 H); 3.55 (m, 1 H), 3.74 (m, 3H), 3.93 (m, 1 H); 4.18 (m, 1 H), 4.34 (m, 1 H), 4.57 (d, 1 H, J = 11.8 Hz), 4.65 (m, 2 H), 5.01 (m, 2 H), 6.04 (d, 1 H, J = 8.3 Hz), 7.36 (m, 5H). (3) .- In the same manner as described in example 4- (7), 920 mg, 0.76 mmol) of the compound prepared in (2) above was deprotected in 20 ml of 90% aqueous AcOH and then treated with 0.075 ml (0.92 mmol) of pyridine and 200 mg (0.84 mmol) of 2,2,2-trichloro-1,1-dimethylethyl chloroformate in methylene chloride, followed by 0.24 ml (1114 mmol) of diphenyl chlorophosphate 0.21 ml (1.52 mmol) of triethylamine and 50 mg of catalytic 4-pyrrolidinopyridine to give 1.03 g (83%) of 3-benzyloxy- (S) -2 - [(R) -3-heptanoyloxytetradecanoylamino] propyl- 2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-heptanoyloxy-tetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2 , 2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as a colorless amorphous solid.

NMR with 1 h (CDCl 3) delta 0.87 (t, 12 H, J = 6.3 Hz), 1.1-1.6 (m, 56 H), 1.78 (s, 3 H), 1.86 (s, 3 H), 2.01 (m, 1 H) , 2.18 (m, 3H), 2.40 (m, 2H), 2.67 (m, 1H); 2.88 (d, 1H, J = 6.5 Hz), 297 (d, 1H, J = 6.9 Hz), 3.41 (m, 2H), 3.72 (m, 1H), 3.82 (m, 1H), 4.24 (m, 1H ); 4.42 (d, 1H, J = 11.8 Hz), 4.64 (m, 3H); 5.16 (m, 1 H), 4.39 (m 2 H), 5.75 (d, 1H, J = 4.3 Hz), 6.05 (d, 1 H, J = 8.4 Hz), 7.22 (m, 15H). (4) .- In the same manner as described in Example 2- (7), 1.0 g (0.61 mmol) of the compound prepared in (3) above was deprotected with 2.0 g (31 mmol) of zinc and acylated with 260 mg (0.73 mmol) of (R) -3-heptanoyloxytetadecanoic acid, in the presence of 220 mg (0.88 mmol) of EEDQ to give 203 mg (21%) of 3-benzyloxy- (S) -2 - [(R) -3-heptanoyloxytetradecanoylamino] propyl-2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-heptanoyloxytetradecanoylamino] -3-0 - [(R) -3-heptane-yloxytetradecanoyl] -β-D -glucopyranoside, as a colorless amorphous solid. (5) .- In the same way as described in example 2- (8), 203 mg (0.13 mmol) of the compound prepared in (4) above was hydrogenated, in the presence of 100 mg of palladium hydroxide on carbon in 10 ml of EtOH and 200 mg of platinum oxide in EtOH / AcOH (10: 1) , to produce 39 mg (21%) of the triethylammonium salt of 3-hydroxy- (S) -2 - [(R) -3-heptanoyloxytetradecanoylamino] propyl-2-deoxy-4-0-phosphono-2 - [( R) -3-heptanoyloxytetradecanoylamino] -3-0 - [(R) -3-heptanoyloxy-tetradecanoyl] -β-D-glucopyranoside, as a white powder; p.f. 171-172 ° C.

IR (film) 3305, 2955, 2924, 2853, 1734, 1644, 1553, 1466, 1377, 1170, 1102, 1052, 722 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (m, 18H), 1.1 -1.7 (m, 93H), 2.2-2.7 (m, 12H), 3.06 (c, 6H, J = 7.1 Hz), 3.3-4.0 (m, 13H), 4.23 (c, 1H, J = 9.3 Hz), 4.43 (d, 1H, J = 8.2 Hz), 5.0-5.3 (m, 4H), 7.30 (d, 1H, J = 8.5 Hz), 7.43 (d, 1H, J = 8.5 Hz). NMR with 13C (cdcL3) ) DELTA 173.8, 173.5, 173.2, 170.8, 170.5, 170.2, 101.0, 77.2, 75.5, 73.1, 71.6, 71.1, 70.9, 70.6, 67.8, 61.6, 60.8, 54.4, 50.5, 45.8, 41.6, 41.4, 39.5, 34.6, 34.4, 32.031.6, 29.8, 29.6, 29.4, 28.9, 25.4, 25.1.22.7.22.6, 14.1.8.6 Analysis calculated for C78Hi5oN3O? 8P.H2 ?: C, 63.86; H, 10.44; N, 2.86; P, 2.11; Found: C, 63.47; H, 10.20; N, 2.59; P.2.02.

EXAMPLE 10 (B9) PREPARATION PE SALT PE TRIETHYLMONIUM PE 4-HYPROXY- (S) -3 -. (R.- 3-PECANOYLOXITETRAPECANOIL1BUTIL-2-PESOXI-4-O-PHOSPHONO-2- r (R.-3- PECANOYLOXITETRAPECANOILAMINOl-3-Or (R) -3- PECANOILTETRAPECA-NOILI-ß-P-GLUCOPIRANOSIPA (COMPOUND) (I) R. = R? = R3 = n-CaH .gCO: X = Y = O; n = p 1: m = 1 = 0: R¿ = Rs = R? = (1) .- In the same manner as described in Example 4- (3), 3.1 g (5.9 mmol) of the compound prepared in Example 4- (1) and 1.1 g (3.904 mmol) of (R) were coupled. ) -3-allyloxycarbonylamino) -4-benzyloxy-1-butanol, in the presence of 3.0 ml (23.6 mmol) of boron trifluoride, to produce 1.96 g (67%) of 4-benzyloxy- (S) -3- (allyloxycarbonylamino) butyl-2-deoxy-3,4,6-tri-0-acetyl-2- (2,2,2-trichloroethoxycarbonylamino) -β- D-glucopyranoside, as an amorphous solid. In the same way as described in Example 4- (4), it was 1. 8 g (2.43 mmol) of the compound prepared immediately above, in 25 ml of methanol, with 5 ml of ammonium hydroxide and then treated with 25 ml of 2,2-dimethoxypropane and 100 mg of camphor-sulfonic acid, to produce 1.34 g (84%) of 4-benzyloxy- (S) -3- (allyloxycarbonylamino) butyl-2-deoxy-4,6-0-isopropylidin- 2- (2, 2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside. (2) .- In the same manner as described in Example 4- (5), 1.0 g (1.53 mmol) of the compound prepared in (1) above was acylated, with 670 mg (1.68 mmol) of acid (R) -3-decanoyloxytetradecanoic, in the presence of 550 mg (1.85 mmol) of EDC-Mel and 50 mg of 4-pyrrolidinopyridine in 15 ml of methylene chloride, to give 1.03 g (65%) of 4-benzyloxy- (S) - 3- (allyloxycarbonylamino) butyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-decanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbonylamino) -β-D -glucopyranoside, as an amorphous solid.

NMR with 1H (CDCI3) delta 0.88 (t, 6H, J = 6.9 Hz), 1.1-1.6 (m, 34H), 1.37 (s, 3H), 1.47 (s, 3H), 1.85 (m, 2H); 2.28 (t, 2H, J = 7.6 Hz), 2.50 (dd, 1 H, J = 15.1, 6.0 Hz), 2.63 (dd, 1 H, J = 15.1, 6.7 Hz), 3.30 (m, 1 H), 3.49 (m, 4H), 3.68 (t, 1 H, J = 9.4 Hz), 3.77 (t, 1 H, J = 10.4 Hz), 3.92 (m, 3H), 4.54 (m, 5H); 4.69 (m, 2H), 5.1-5.4 (m, 4H), 5.91 (m, 1 H); 7.33 (m, 5H). (3) .- In the same manner as described in example 4- (6), 1.0 g (0.97 mmol) of the compound prepared in (2) above was deprotected in 20 ml of THF, in the presence of 1.0 ml (0.88). mmol) of dimethyl malonate and 200 mg of tetracis- (triphenylphosphine) palladium (0), and then acylated with 425 mg (1.07 mmol) of (R) -3-decanoyloxytetradecanoic acid, in the presence of 317 mg (1.28 mmol) of EEDQ, to produce 660 mg (51%) of 4-benzyloxy- (S) -3 - [(R) -3-decanoyloxytetradecanoylamino-no] propyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-decanoyloxy-tetradecanoyl] -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glycopyranoside, as an amorphous, colorless solid. 1 H NMR (CDCl 3) delta 0.88 (t, 12 H, J = 6.6 Hz), 1.1-1.7 (m, 68H), 1.37 (s, 3H), 1.47 (s, 3H), 2.26 (c, 2H, J = 7.1 Hz), 2.41 (m, 2H), 2.62 (dd, 1 H, J = 14.9, 6.4 Hz) , 3.29 (m, 1 H), 3.48 (m, 3H), 3.71 (m, 2H), 3.92 (m, 2H); 4.18 (m, 1 H), 4.49 (m, 2H), 4.68 (c, 2H, J = 11.5 Hz), 5.15 (m, 2H), 5.55 (d, 1 H, J = 8.8 Hz), 6.17 (d , 1 H, J = 7.2 Hz), 7.32 (m, 5H). (4) .- In the same manner as described in Example 4- (7) 640 mg (0.48 mmol) of the compound prepared in (3) above was deprotected, in 20 ml of 90% aqueous AcOH and treated with 0.047 ml (0.58 mmol) of pyridine and 127 mg (0.53 mmol) of 2,2,2-trichloro-1,1-dimethylethyl chloroformate in methylene chloride, followed by 0.15 ml (0.72 mmol) of diphenyl chlorophosphate, 0.13 ml (0.96 mmol) of triethylamine and 50 mg of catalytic 4-pyrrolidinopyridine, to give 389 mg (47%) of 4-benzyloxy- (S) -3- [ (R) -3-decanoyloxytetradecanoyl] butyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-decanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1, - dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxy-carbonylamino) -β-D-glucopyranoside, as an amorphous, colorless solid. 1 H NMR (CDCl 3) delta 0.88 (t, 12H; J = 6.6 Hz), 1.1-1.6 (m, 68H), 1.79 (s, 3H), 1.86 (s, 3H), 2.22 (m, 4H), 2.40 (m, 4H), 2.40 (m, 4H), 3.49 (m, 4H), 3.78 (m, 1 H), 3.93 (m, 1H), 4.1-4.5 (m, 5H), 4.9-4.6 (m, 4H), 5.13 (m, 2H), 5.51 (t , 1 H, J = 8.9 Hz), 5.84 (d, 1 H, J = 6.9 Hz), 6.09 (d, 1 H, J = 8.0 Hz), 7.26 (m, 15H). (5) .- In the same manner as described in Example 2- (7), 375 g (0.23 mmol) of the compound prepared in (4) above was deprotected with 752 mg (11.5 mmol) of zinc, and acylated with 101 mg (0.25 mmol) of (R) -3-decanoyloxytetradecaneic acid in the presence of 70 mg (0.28 mmol) of EEDQ, to give 270 mg (67%) of 4-benzyloxy- (S) -3 - [( R) -3- decanoyloxytetradecanoyl] -butyl-2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-decanoyloxytetrade-canoylamino] -3-0 - [(R) -3-decanoyltetradecanoyl] -β- D-glucopyranidase, as an amorphous, colorless solid. (6) .- In the same manner as described in example 2- (8), 270 mg (0.15 mmol) of the compound prepared in (5) above was hydrogenated in the presence of 150 mg of palladium hydroxide on carbon in 10%. ml of EtOH and 300 mg of platinum oxide in 10: 1 EtOH / AcOH, to produce 93 mg (39%) of the triethylammonium salt of 4-hydroxy- (S) -3 - [(R) -3-decanoyloxytetradecanoyl] butyl-2-deoxy-4-0-phosphono-2 - [(R) -3- decanoyloxytetradeanoylamino] -3-0 - [(R) -3-decanoyltetradecanoyl] -D-glucopyranoside, as a white powder; p. F. 179-181 ° C (with decomposition). IR (film): 3287, 2956, 2923, 2853, 1734, 1654, 1552, 1466, 1378, 1246, 1164, 1106, 1085, 1052, 721 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.9 Hz9, 1.1-1.7 (m, 111H), 2.2-2.7 ( m, 14H), 3.06 (c, 6H, J = 6.9 Hz), 3.2-4.0 (m, 13H), 4.21 (m, 1H), 4.50 (d, 1H, J = 7.7 Hz), 5.0-5.3 (m , 4H), 7.11 (m, 2H). NMR with 13C (CDCI3) delta: 173.8, 173.5, 173.3, 170.9, 170.5, 170.1, 101.1, 77.2, 75.5, 72.8, 71.3, 71.0, 70.6, 66.4, 64.0, 60.7 , 54.8, 50.2, 45.8, 41.6, 39.5, 34.6, 34.5, 34.4, 32.0, 30.6, 29.8, 29.7, 29.6, 29.5, 29.4, 25.4, 25.4, 25.1, 22.7, 14.2, 8.6 Analysis calculated for C88H? 70N3O? 8P: C , 66.65; H, 10.78; N, 2.65; P, 1.95; Found: C, 66.65; H, 10.68; N, 2.50; P, 1.94; EXAMPLE 11 (B10) PREPARATION PE SALT PE TRIETHYLAMINE PE 4-HYPROXY- (S) -2 -. (R.-3- PECANOYLOXITETRAPECANOlL1BUTIL-2-PESOXY ~ 4-O-PHOSPHONO-rr (R) -3- PECANOYLOXITETRAPECANOILAMINO1- 3-Or (R) -3-PECANOYLTETRA-PECANOILI-ß-P-GLUCOPYRANOSIPA (COMPOUND (I); R. = R? = R, g n- CQH. QCQ: X = Y = O; n = m = q = 0; R? = Rs = R7 = RQ = H: Rfi = OH: p = 2: R »= OsH ,, (1) .- In the same manner as described in Example 4- (3), 5.1 g (9.7 mmol) of the compound prepared in Example 4- (1) and 1.8 g (6.45 mmol) of (R) were coupled. -2- (allyloxycarbonylamino) -4-benzyloxy-1-butanol, in the presence of 4.9 ml (38.0 mmol) of boron trifluoride etherate, to yield 2.92 g (61%) of 4-benzyloxy- (S) -2- (allyloxycarbonylamii-no) propyl-2-deoxy-3,4,5-tri-0-acetyl-2- (2,2,2-trichloroethoxy-carbonylamino) -β-D-glucopyranoside, as an amorphous solid. In the same manner as described in Example 4- (4) - 2.6 g (3.51 mmol) of the compound prepared immediately above was dissolved in 35 ml of methanol with 7 ml of ammonium hydroxide, and then treated with 35 ml of methanol. ml of 2,2-dimethoxypropane and 100 mg of camphorsulfonic acid, for ar 1.9 g (72%) of 4-benzyloxy- (S) -2- (allyloxycarbonylamino) butyl-2-deoxy-4,6-0-isopropylidin- 2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside. (2) .- In the same manner as described in Example 4- (5), 1.0 g (1.53 mmol) of the compound prepared in (1) above was acylated, with 670 mg (1.68 mmol) of acid (R) -3-decanoyloxytetradecanoic, in the presence of 550 mg (1.85 mmol) of EDC.Mel and 50 mg of 4-pyrrolidinopyridine in 15 ml of methylene chloride, to give 1.28 g (81% of 4-benzyloxy- (S) -2 - (allyloxycarbonylamino) butyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-decanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbonyl-amino) -β-D- glucopyranoside, as an amorphous solid.

NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.9 Hz), 1.1-1.7 (m, 34H), 1.37 (s, 3H), 1.47 (s, 3H); 1.82 (m, 2H), 2.28 (t, 2H, J = 7.7 Hz), 2.50 (dd, 1 H, J = 15.3, 6.0 Hz), 2.63 (dd, 1 H, J = 15.2, 6.7 Hz), 3.16 (m, 1 H), 3.56 (m, 3H); 3.65 (t, 1 H, J = 9., 6 Hz), 3.75 (t, 1 H, J = 10.4 Hz), 3.88 (m, 4H), 4.32 (d, 1 H, J = 8.5 Hz), 4.46 (s, 2H), 4.54 (m, 2H); 4.67 (m, 2H), 4.90 (m, 1 H), 5.26 (m, 3H), 5.89 (m, 1 H); 7.33 (m, 5H). (3) .- In the same manner as described in Example 4- (6), 1.25 g (1.21 mmol) of the compound prepared in (2) above was deprotected in 20 ml of THF, in the presence of 1.0 ml (0.88). mmol) of dimethyl malonate and 200 mg of tetracis- (triphenylphosphine) palladium (0), and then acylated with 530 mg (1.33 mmol) of (R) -3-decanoyloxytetradecanoic acid, in the presence of 362 mg (1.46 mmol) of EEDQ, to produce 1.16 g (72%) of 4-benzyloxy- (S) -3 - [(R) -3-decanoyloxytetradecanoylamino-no] propyl-2-deoxy-4,6-0-isopropylidene-3-0 - [(R) -3-decanoyloxy-tetradecanoyl] -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glycopyranoside, as an amorphous, colorless solid.

NMR with 1H (CDCl 3) delta 0.88 (t, 12H, J = 6.4 Hz), 1.1-1.7 (m, 68H), 1.37 (s, 3H), 1.45 (s, 3H), 2.26 (c, 2H, J = 7.4 Hz), 2.34 (m, 1 H); 2.50 (dd, 1 H, J = 15.1, 6.0 Hz), 2.62 (dd, 1 H, J = 15.4, 6.3 Hz), 3.12 (m, 1H), 3.5- 3.95 (m, 7H); 4.14 (m, 1 H), 4.29 (d, 1 H, J = 8.0 Hz), 4.67 (m, 2H), 4.86 (t, 1 H, J = 9.6 Hz), 5.15 (m, 2H), 6.16 ( d, 1 H, J = 8.3 Hz), 7.35 (m, 5H). (4) .- In the same manner as described in example 4- (7), 1.1 g (0.83 mmol) of the compound prepared in (3) above was deprotected in 20 ml of 90% aqueous AcOH, and then treated with 0.080 ml (1.0 mmol) of pyridine and 220 mg (0.91 mmol) of 2,2,2-trichloro-1,1-dimethylethyl chloroformate in methylene chloride, followed by 0.26 ml (1.25 mmol) of chlorophosphate. diphenyl, 0.23 ml (1.66 mmol) of triethylamine and 50 mg of catalytic 4-pyrrolidinopyridine, to yield 802 mg (56%) of 4-benzyloxy- (S) -2 - [(R) -3-decanoyloxytetradecanoyl] buyl -2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-decanoyloxytetrade-decanoyl] -6-0- (2,2,2-trichloro-1,1-dimethoxycarbonyl) -2 - (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as an amorphous, colorless solid. NMR with 1 H (CDCl 3) delta 0.87 (t, 12 H, J = 6.8 Hz), 1.1-1.6 (m, 68 H), 1.79 (s, 3 H), 1.88 (s, 3 H), 2.23 (m, 4 H), 2.37 (m, 4H), 3.57 (m, 4H), 3.83 (m, 1H), 4.29 (m, 3H), 4.44 (m, 2H), 4.69 (m, 4H), 5.14 (m, 4H), 5.62 (d, 1 H, J = 7.6 Hz), 6.15 (d, 1 H, J = 8.3 Hz), 7.25 (m, 15H). (5) .- In the same manner as described in Example 2- (7), 750 mg (0.43 mmol) of the compound prepared in (4) above was deprotected with 1.42 g (21.7 mmol) of zinc and acylated with 190 mg (0.48 mmol) of (R) -3-decanoyloxytetrade-canoic acid in the presence of 130 mg (0.53 mmol) of EEDQ to produce 483 mg (64%) of 4-benzyloxy- (S) -2 [(R) -3-decanoyloxyte-tradecanoyl] butyl-2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-decanoyl oxytetradecanoylamino] -3-0 - [(R) -3-decanoyltetradecanoyl] -β-D- glucopyranoside, as an amorphous, colorless solid. (6) .- In the same manner as described in example 2- (8), 483 mg (0.27 mmol) of the compound prepared in (5) above was hydrogenated in the presence of 150 mg of palladium hydroxide on carbon, in 10 ml of EtOH and 300 mg of platinum oxide in EtOH / AcOH (10: 1), to yield 238 mg (55%) of the triethylammonium salt of 4-hydroxy- (S) -2 - [(R) -3-decanoyloxytetradecanoyl] butyl-2-deoxy-4-0-phosphono-2 - [(R) -3-decanoyloxytetradecanoylamino] -3-0 - [(R) -3-decanoyltetradeca-noyl] -β-D-glucopyranoside , like a white powder, p. F. 181-183X (with decomposition). IR (film) 3294, 2956, 2923, 2853, 1732, 1650, 1466, 1377, 1320, 1246, 1172, 1108, 1082, 1058, 859, 721 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 ( t, 18H, J = 6.9 Hz), 1.1-1.7 (m, 111 H), 2.2-2.7 (m, 14H), 3.06 (c, 6H, J = 7.1 Hz), 3.2-4.0 (m, 13H), 4.21 (m, 1 H), 4.46 (d, 1 H, J = 8.3 Hz), 5.0-5.3 (m, 4H). NMR con13C (CDCI3) delta 173.9, 173.4, 173.2, 171.2, 170.7, 101.0, 77.2, 75.4, 73.1, 71.4, 71.3, 71.1, 70.9, 70.6, 60.7, 58.4, 54.7, 46.8, 45.9, 41.6, 41.1, 39.7, 34.8, 34.6, 34.4, 34.4, 31.9, 29.8, 29.6, 29.5, 29.3, 29.3, 29.3, 29.3, 29.3, 29.3 25.1, 22.7, 14.1, 8.6.

Analysis calculated for C85H? 7oN3O? 8P: C, 66.51; H, 10.78; N, 2.64; P, 1.95; Found: C, 66.81; H, 10.68; N, 2.53; P, 1.79.

EXAMPLE 12 (B11) PREPARATION triethylammonium PE PE PE SALT Nf (R) -3- TETRAPECANOILOXITETRAPECANOIL1-O-r2-PESOXI-4-o-phosphono-2- r (R-3-TETRAPECANOILOXITETRAPECANOILAMINO1-3-Or (R) -3- TETRAPECANOILOXITETRAPECANOILI-ß-P-GLUCOPIRANOSILI-L-serine (COMPOUND (I), Ri = R2 = R, = nC aH27CO; g g Q; n = m = 0 pgqg:? R = Rs g R? ? = RQ = CO? H; R «= O ^ H?) (1) .- In the same manner as described in example 2- (5), 0.212 g (1.08 mmol) of the benzyl ester of L-serine was acylated with 0.541 g (1.19 mmol) of acid (R) -3. -tetradecanoi -loxitetradecanoico in the presence of 0.353 g (1.19 mmol) of EDC-Mel to give 0.642 g (94%) benzyl ester N - [(R) -3-tetradecanoyloxytetradecanoyl] -L-serine, as a solid Waxy p. F. 56-61 ° C. NMR with 1H (CDCI3) delta 0.88 (t, 6H, J = 7 Hz), 1.1-1.7 (m, 42H), 2.29 (t, 2H, J = 7.5 Hz), 2.50 (m, 2H), 3.87 (t broad, 1 H), 3.95 (m, 2H), 4.65 (m, 1 H), 5.1-5.25 (m, 3H), 6.69 (d, 1 H, J = 7 Hz), 7.34 (broad s, 5H) . (2) .- In the same manner as described in Example 2- (6), 0.19 g (0.30 mmol) of the compound prepared in (1) above was coupled, and 0.635 g (0.478 mmol) of the compound prepared in the Example 2- (4), in the presence of 0.3 g (1.2 mmol) of mercuric cyanide, to give 0.425 g (77%) of the benzyl ester of N - [(R) -3-tetradecanoyloxytetradecanoyl] -0- [2-des] -oxi-4-0-diphenylphosphono-3-0 - [(R) -3-tetradecanoyloxytetradeca-noyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2, 2,2-trichloroethoxycarbonylamino) -β-D-glucopyranosyl] -L-serine, as an amorphous solid. (3) .- In the same manner as described in Example 2- (7), 0.405 g (0.22 mmol) of the compound prepared in (2) above was deprotected with 0.72 g (11 mmol) of zinc, and acylated with 0.12 g (0.26 mmol) of (R) -3-tetradecanoyloxy-tetradecanoic acid in the presence of 0.082 g (0.33 mmol) of EEDQ to give 0.277 g (66%) of the benzyl ester of N - [(R) -3-tetradecanoi -loxitetradecanoil] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -3-0 - [(R) -3-tetradecanoyloxy -tetradecanoyl] -ß-D-glucopyranosyl ] -L-serine, as an amorphous solid. NMR with 1H (CDCI3) delta 0.88 (t, 18H, J = about 6.5 Hz), 1. 0-1.75 (m, 126H), 2.15-2.45 (m, 10H), 2.53 (dd, 1 H, J = 14.7, 6.0 Hz), 2.67 (dd, 1 H, J = 14, 6.0 Hz), 3.2 ( t broad, 1 H, J = 7 Hz), 3.35-3.75 (m, 4H), 3.88 (dd, 1 H, J = 11.1 Hz), 4.23 (dd, 1 H, J = 11, 1.3 Hz), 4.6 -4.75 (m, 2H); 5.03 (d, 1 H, J = 8.1 Hz), 5.05-5.25 (m, 4H), 5.48 (t, 1 H, J = about 10 Hz), 6.40 (d, 1 H, J = 7.5 Hz); 7.01 (d, 1 H, J = 8.1 Hz), 7.1-7.4 (m, 15H). (4) .- In the same manner as described in example 2- (8), 0.253 g (0.133 mmol) of the compound prepared in (3) above was hydrogenated in the presence of 50 mg of 5% palladium on carbon and 120 mg of platinum oxide, to give 0.155 g (62%) of the triethylammonium salt of N - [(R) -3-tetradecanoyloxytetradecanoyl] -0- [2-deoxy-4-0-phosphono-2 - [( R) -3-tetradecanoyloxytetradecanoyl] -β-D-glucopyranosyl [-L-serine, as a colorless solid, e.g. F. 180 ° C (decomposition). IR (film) 3322, 2956, 2924, 2852, 1736, 1732, 1681, 1673, 1667, 1660, 1651, 1467, 1456, 1247, 1174, 1110, 1081 cm. "1 NMR with 1H (CDCI3-CD3OD) delta? .88 (t, 18H, J = about 7 Hz), 1.0-1.7 ( m, 135H), 2.2-2.75 (m, 12H), 3.05 (c, 6H, J = 7 Hz), 3.30 (broad s, 13H), 3.7-3.9 (m, 3H), 3.96 (d, 1H, J = 12 Hz), 4.05-4.3 (m, 2H), 4.34 (m, 1 H), 4.53 (d, 1 H, J = 7.8 Hz), 5.05-5.3 (m, 4H), 7.25-7.35 (m , 2H). NMR with 13 C (CDCl 3) delta 173.4, 173.2, 171.0, 170.3, 170.2, 169.9, 169.8, 100.8, 75.1, 73.4, 71.1, 70.7, 70.4, 70.3, 60.2, 54.3, 45.6, 41.2, 41.1, 39.2 , 34.6, 34.4, 34.2, 32.0, 29.8, 29.5, 25.4, 25.2, 22.7, 14.2, 8.6 Analysis calculated for C99H? 90N3O? 9P.5H2 ?: C, 64.35; H, 10.91; N, 2.27; P, 1.68; Found: C, 64.16; H, 10.92; N, 2.37; P, 1.91.

EXAMPLE 13 (B12) PREPARATION triethylammonium PE PE PE SALT N-HR.-3- POPECANOILOXITETRAPECANOIL1-O-r2-PESOXI-4-o-phosphono-2-r (3-A.- POPECANOILOXITETRAPECANOILAMINO1-3-or (R) -3- POPECANOILOXI-TETRAPECANOILI-ß-P-GLUCOPIRANOSILM-SERINE (COMPOUND (I), Rjg R7 = R3 = n> 1H23CO, X = Y = O: n g m = p = q = 0: R4 g Rs = R7 = Rg = H, Rg = CO2H, Ra - POgH2 (1) .- In the same manner as described in example 2- (5), 390 mg (2.0 mmol) of the benzyl ester of L-serine was acylated with 935 mg (2.2 mmol) of acid (R) -3. -dodecanoiloxitetradecanoico, in the presence of 745 mg (2.5 mmol) of EDC-Mel in methylene chloride, to give 1.08 g (90%) of the benzyl ester of N - [(R) -3-dodecanoyloxytetradecanoyl] -L-serine, m.p. 53-54 ° C. NMR with 1H (CDCI3) delta 0.88 (t, 6H, J = 6.5 Hz), 1.1-1.6 (m, 46H), 2.30 (t, 2H, J = 7.7 Hz), 2.50 (d, 2H, J = 5.6 Hz ), 2.62 (t, 1 H, J = 6.2 Hz), 3. 97 (m, 2H), 4.65 (m, 1 H), 5.19 (m, 3H); 6.63 (d, 1 H, J = 6.8 Hz), 7.35 (broad s, 5H). (2) .- In the same manner as described in Example 2- (2), 1.0 g (2.02 mmol) of the compound prepared in Example 2- (1) was acylated with 946 mg (2.22 mmol) of acid ( R) -3-dodecanoiloxytetradecanoic, in the presence of 720 mg (2.4 mmol) of EDC.Mel and 100 mg of 4-pyrrolidinopyridine, in methylene chloride; and then deprotected in 25 ml of aqueous AcOH to give 1.30 g (81%) of 2- (trimethylsilyl) ethyl-2-deoxy-3-0 - [(R) -3-dodecanoyloxytetradecanoyl] -2- (2.2 , 2-trichloroethoxycarbo-nylamino) -β-D-glucopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.00 (s, 9H), 0.88 (m, 8H), 1.25 (m, 28H), 1.59 (m, 4H), 2.30 (t, 2H, J = 7.5 Hz), 2.52 (m, 2H), 3.42 (m, 1 H), 3.55 (m, 1 H), 3.66 (m, 1 H); 3.83 (dd, 1 H, J = 11.8, 4.6 Hz), 3.94 (m, 2H), 4.57 (d, 1 H, J = 8.2 Hz), 4.71 (m, 2H), 5.07 (m, 2H), 5.27 (d, 1 H, J = 8.8 Hz). (3) .- In the same manner as described in Example 2- (3), 1.30 g (1.51 mmol) of the compound prepared in (2) above was treated with 398 mg (1.66 mmol) of chloroformate of 2.2. , 2-trichloro-1,1-dimethylethyl and 0.15 ml (1.83 mmol) of pyridine in 25 ml of methylene chloride, followed by 0.42 ml (3.02 mmol) of triethylamine, 0.47 ml (2.27 mmol) of diphenyl chlorophosphate and 100 mg of 4-pyrrolidinopyridine, to yield 1.39 g (71%) of 2- (trimethylsilyl) ethyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-dodecanoyloxytetradecanoyl] -6-0 - (2,2,2-trichloro-1,1-dimethyl-ethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glycopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.0 (s, 9H), 0.88 (m, 8H), 1.1-1.7 (m, 46H), 1.77 (s, 3H), 1.85 (s, 3H), 2.23 (m, 6H), 3.34 (m, 1 H), 3.59 (m, 1 H), 3.80 (m, 1H), 3.96 (m, 1H), 4.32 (m, 2H), 4.63 (m, 2H), 4.83 (d, 1H, J = 11.9 Hz), 5.02 (d, 1 H, J = 8.2 Hz ), 5.20 (m, 1 H), 5.65 (m, 2H); 7.29 (m, 10H). (4) .- treated 1.30 g (1.0 mmol) of the compound prepared in (3) above, in 15 ml of methylene chloride, at 0 ° C, with 5 ml of TFA, and then allowed to warm to room temperature for 18 hours. The solvent was removed in vacuo and the remaining TFA was removed by azeotroping with toluene. The lactol was treated with the Vismeier reagent, prepared from 0.39 ml (5.0 mmol) of DMF and 0.22 ml (2.5 mmol) of oxalyl chloride in 20 ml of methylene chloride, at 0 ° C. The reaction was allowed to slowly warm to room temperature overnight, and was partitioned between 50 ml of saturated aqueous sodium bicarbonate and 50 ml of ether. The layers were separated and the organic phase was dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel with 10% EtOAc / hexanes afforded 1.09 g (90%) of 2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-dodecanoyloxytetradecanoyl] chloride. 6-0- (2,2, 2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -alpha-D-glucopyranosyl, as a white foam. NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.8 Hz), 1.2-1.70 (m, 46 H), 1.78 (s, 3H), 1.88 (s, 3H), 2.18 (t, 2H, J = 7.7 Hz), 2.43 (m, 2H), 4.30 (m, 4H), 4.72 (m, 3H), 5.09 (m, 1 H); 5.50 (t, 1 H, J = 9.5 Hz), 5.79 (d, 1 H, J = 8.0 Hz), 6.27 (d, 1H, J = 3.6 Hz), 7.19 (m, 10H). (5) .- To a solution of 540 mg (0.90 mmol) and 1.0 g (0.82 mmol), respectively, of the compounds prepared in (1) and (4), in 20 ml of 1,2-dichloroethane, was added 300 mg of molecular sieves sprayed at 4Á and the suspension was stirred for 30 minutes. 1.16 g (4.5 mmol) of AgOTf was added in one portion.; after 30 minutes the suspension was filtered through silica gel and eluted with 30% EtOAc / hexanes to give 1.10 g (75%) of the benzyl ester of N - [(R) -3-dodecane-iloxytetradecanoyl] - 0- [2-deoxy- -0-diphenylphosphono-3-0 - [(R) -3-dodecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethylcarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyrene-nosyl] -L-serine. NMR with 1H (CDCl 3) d 0.88 (t, 12H, J = 6.5 Hz), 1.1-1.65 (m, 92H), 1.77 (s, 3H), 1.85 (s, 3H), 2.1-2.5 (m, 8H, 3.67 (m, 2H), 4.30 (m, 3H), 4.72 (m, 5H), 5.18 (m, 4H), 5.46 (m, 1 H), 6.07 (m, 1 H), 6.62 (d, 1 H) J = 7.9 Hz), 7.05-7.45 (m, 15H). (6) .- In the same manner as described in Example 2- (7), 1.0 g (0.56 mmol) of the compound prepared in ( 5) above with 1.83 g (28 mmol) of zinc, and acylated with 285 mg (0.67 mmol) of (R) -3-dodecanoyloxytetra-decanoic acid in the presence of 185 mg (0.74 mmol) of EEDQ to yield 420 mg ( 44%) of the benzyl ester of N - [(R) -3-dodecanoyloxytetradecanoyl] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-dodecanoyloxytetradecanoylamino] -3-0 - [( R) -3-dodecanoyl-oxytetradecanoyl] -β-D-glucopyranosyl] -L-serine, as an amorphous solid. (7) .- In the same manner as described in example 2- (8), 420 was hydrogenated mg (0.24 mmol) of the compound prepared in (6) above, in the presence of palladium hydroxide on carbon in 10 ml of EtOH and 400 mg platinum oxide in 10: 1 EtOH / AcOH, to produce 240 mg (60%) of the ammonium salt of N - [(R) -3-dodecanoyloxytetradecanoyl] -0- [2-deoxy] 4-0_phosphon-2 - [(R) -3-dodecanoyloxytetradecanoylamino] -3-0 - [(R) -3-dodecanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L-serine, as a white powder, e.g. F. 181-182 ° C.

IR (film) 3289, 2956, 2920, 2851, 1731, 1656, 1557, 1467, 1378, 1182, 1108, 1080, 1052, 852, 721 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.7 Hz), 1.1-1.7 (m, 123H), 2.2-2.7 (m, 12H), 3.06 (c, 6H, J = 7.2 Hz), 3.35 (m, 1H), 3.70 (m, 6H), 3.88 (m, 2H), 4.20 (m, 1 H), 4.56 (d, 1 H, J = 8.1 Hz), 4.59 (s broad 1 H), 5.16 (m, 4H), NMR with 13C ( CDCI3) delta 176.9, 173.3, 173.2, 172.7, 169.6, 169.1, 101.5, 74.8, 71.2, 70.9, 69.2, 60.5, 53.1, 51.4, 46.1, 41.5, 41.0, 39.2, 34.3, 34.2, 34.0, 32.0, 29.8, 29.7 , 29.4, 29.2, 25.6, 25.3, 25.2, 25.1, 22.7, 14.1, 8.7, Analysis calculated for C93HHSN3O19P.H2O: C, 66.04; H, 10.73; N, 2.48; P, 1.83; Found: C, 66.04; H, 10.73; N, 2.48; P, 1.86.

EXAMPLE 14 (B13) PREPARATION PE SALT PE TRIETILAMONIO PE N-KR.-3-UNPECANOIL-OXlTETRAPECANOlL1-O-r2-PESOXI-4-O-PHOSPHONO-2 -. (R.- 3-UNPECANOIL-TETRAPECANOILAMINO1-3-Or (R) - 3- UNPECANOILOXITETRAPECANOILl-ß-P-GLUCOPIRANOSILI-L-SERINA (COMPOUND (I), Ri = R? = R, = nC? OH? CO: X = Y = O; n = m = p = q = 0: R4 s Rs = R7 = Rg = H; Re = CO2H; R »= ¡PO3H2) (1) .- In the same manner as described in Example 2- (5), 390 mg (2.0 mmol) of the benzyl ester of L-serine was acylated with 905 mg (2.2 mmol) of acid (R) -3. -undecanoiloxitetradecanoico, in the presence of 745 mg, 2. 5 mmol) of EDC-Mel in methylene chloride, to give 1.08 g (92%) of the benzyl ester of N - [(R) -3-undecanoyloxytetradecanoyl] -L-serine; p.f. 53-54 ° C.

NMR with H (CDCI3) delta 0.88 (t, 6H, J = 6.9 Hz), 1.1-1.7 (m, 44H), 2.30 (t, 2H, J = 7.7 Hz), 2.49 (d, 2H, J = 5.8 Hz ), 3.99 (m, 2H), 4.65 (m, 1 H), 5.19 (m, 3H); 6.58 (d, 1 H, J = 6.9 Hz), 7.35 (broad s, 5H). (2) .- In the same manner as described in Example 2- (2), 1.0 g (2.02 mmol) of the compound prepared in Example 2- (1) was acylated with 915 mg (2.22 mmol) of acid ( R) -3-undecanoyloxytetradecanoic, in the presence of 720 mg (2.4 mmol) of EDC-Mel and 100 mg of 4-pyrrolidinopyridine in methylene chloride, and then deprotected in 25 ml of aqueous AcOH to give 1.41 g (82%) 2- (Trimethylsilyl) ethyl-2-deoxy-3-0 - [(R) -3-undecanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbo-nylamino) -β-D-glucopyranoside, as an amorphous solid . NMR with 1H (CDCI3) delta 0.00 (s, 9H), 0.88 (m, 8H), 1.25 (m, 32H), 1.60 (m, 4H), 2.31 (t, 2H, J = 7.5 Hz), 2.62 (m , 2H), 3.42 (m, 1H), 3.55 (m, 1H), 3.66 (m, 1 H), 3.83 (dd, 1 H, J = 11.8, 4.6 Hz), 3.94 (m, 2H); 4.57 (d, 1H, J = 8.2 Hz), 4.71 (m, 2H), 5.07 (m, 2H), 5.27 (d, 1H, J = 8.7 Hz). (3) .- In the same manner as described in Example 2- (3), 1.30 g, 1.53 mmol) of the compound prepared in (2) above was treated, with 403 mg (1.68 mmol) of chloroformate of 2, 2,2-trichloro-1,1-dimethylethyl and 0.15 ml (1.85 mmol) of pyridine in 25 ml of methylene chloride, followed by 0.43 ml (3.06 mmol) of triethylamine, 0.48 ml (2.30 mmol) of diphenyl chlorophosphate and 100 mg of 4-pyrrolidino-pyridine, to give 1.37 g (70%) of 2- (trimethylsilyl) ethyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-undecanoyloxytetradeca-noyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.0 (s, 9H), 0.88 (m, 8H), 1.1-1.7 (m, 44H), 1.80 (s, 3H); 1.89 (s, 3H), 2.23 (m, 6H), 3.58 (m, 3H), 4.32 (m, 1H), 4.71 (m, 2H), 4.83 (d, 1 H, J = 12.1 Hz), 5.01 ( d, 1H, J = 8.1 Hz), 5.20 (m, 1H), 4.62 (m, 2H), 7.25 (m, 10H). (4) .- In the same manner as described in example 13- (4) 1.28 g (1.0 mmol) of the compound prepared in (3) above was deprotected with 5 ml of TFA and then treated with the reagent from Vilsmeier, generated from 0.39 ml (5.0 mmol) of DMF and 0.22 ml (2.5 mmol) of oxalyl chloride, to give 1.12 g (93%) of 2-deoxy-4-0-diphenylphosphono-3-chloride -0 - [(R) -3-undecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-di-methylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -alpha-D -glucopyranosyl, as a white foam. NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.7 Hz), 1.1-1.55 (m, 44H), 1.78 (s), 3H), 1.88 (s, 3H), 2.18 (m, 2H), 2.43 (m, 2H), 4.34 (m, 4H), 4.72 (m, 3H), 5.09 (m, 1 H), 5.50 (t , 1 H, J = 9.6 Hz), 5.80 (d, 1 H, J = 8.0 Hz), 6.26 (d, 1 H, J = 3.4 Hz), 7.26 (m, 10H). (5) .- In the same manner as described in example 13- (5), 530 mg (0.90 mmol) and 1.0 g (0.83 mmol), respectively, of the compounds prepared in (1) and (4) were coupled. ) above, in the presence of 1.16 g (4.5 mmol) of AgOTf, to produce 1.11 g (76%) of the benzyl ester of N - [(R) -3-undecanoyloxytetradecanoyl] -0- [2-deoxy-4-0- diphenylphosphono-3-0 - [(R) -3-undecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-di-methylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) - β-D-glucopyranosyl] -L-serine. 1 H NMR (CDCl 3) delta 0.88 (m, 12H), 1.0-1.65 (m, 88H), 1.77 (s, 3H), 1.85 (s, 3H), 2.1-2.5 (m, 8H), 3.37 (m, 1 H), 3.64 (m, 1 H), 3.85 (m, 1 H), 4.30 (m, 3 H), 4.78 (m, 5 H), 5.18 (m, 4 H), 5.46 (m, 1 H), 6.07 (m, 1 H), 6.62 (d, 1 H, J = 7.7 Hz), 7.05-7.45 (m, 15H). (6) .- In the same manner as described in Example 2- (7), 1.0 g (0.57 mmol) of the compound prepared in (5) above was deprotected with 2.0 g (30.5 mmol) of zinc and acylated with 280 mg (0.68 mmol) of (R) -3-undecanoyloxytetra-decanoic acid in the presence of 185 mg (0.75 mmol) of EEDQ, to yield 470 mg (50%) of the benzyl ester of N - [(R) -3 -undecanoiloxitetradecanoil] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-undecanoyloxytetradecanoylamino] -3-0 - [(R) -3-undecanoyl-oxitetradecanoil] -ß-D-glucopyranosyl ] -L-serine, as an amorphous solid. (7) .- In the same manner as described in example 2- (8), 470 mg (0.27 mmol) of the compound prepared in (6) above was hydrogenated, in the presence of palladium hydroxide on carbon in 10 ml of EtOH and 400 mg of platinum oxide in 10: 1 EtOH / AcOH to yield 130 mg (30%) of the triethylammonium salt of N - [(R) -3-undecanoiloxitetradecanoil] -0- [2-des- oxy-4-0-phosphono-2 - [(R) -3-undecanoyloxytetradecanoylamino] -3-0 - [(R) -3-undecanoiloxitetradecanoil] -ß-D-glucopyranosyl] -L-serine as a white powder, p . F. 181-183 ° C. IR (film) 3294, 2923, 2853, 1734, 1655, 1466, 1377, 1163, 1080, 721 cm "1. 1H NMR (CDCl3-CD3OD) delta 0.88 (t, 18H, J = 6.8 Hz), 1.1- 1.7 (m, 117H), 2.2-2.7 (m, 12H); 3.06 (c, 6H, J = 7.1 Hz), 3.4-3.2 (m, 5H), 3.6-3.9 (m, 4H), 4.20 (d, 1 H, J = 9.8 Hz), 4.54 (d, 1 H, J = 8.0 Hz), 4.62 (broad s, 1 H); 5.17 (m, 4H). NMR with 13C (CDCI3) delta 173.5, 173.3, 172.8, 172.2, 169.6, 169.1, 101.5, 77.2, 74.8, 70.9, 69.2, 60.5, 58.5, 53.1, 51.5, 46.1, 41.5, 41.1, 39.2, 34.6, 34.4, 34.1 , 32.0, 29.8, 29.7, 29.4, 29.2, 25.6, 25.2, 25.1, 22.7, 18.5, 14.2, 8.7.

Analysis calculated for C9oH? 72N3019P: C, 66.26; H, 10.63; N, 2.58; P, 1.90; Found: C, 66.56; H, 10.57; N, 2.47; P, 1.91.

EXAMPLE 15 (B14) PREPARATION OF THE TRIETHYLMONIUM SALT OF Nf (R) -3- DECANOYLOXI-TETRAPECANOIL1-O-r2-DESOXY-4-O-PHOSPHONO-2-r (R.-3- PECANOYLOXITETRAPECANOILAMINO1-3-Or ( R -3-PECANOYLOXY- TETRAPECANOILI-ß-P-GLUCOPYRANOSILI-P-SERINE (COMPOUND (I) Ri = R; = R_ = n-CaH .gCO: X = Y = O; n = m = p = q = 0, R. = RR = R7 = R <? = H; Rfi g CO? H ?; R »- POrtO ?. (1) .- In the same manner as described in example 2- (5), 390 mg (2.0 mmol) of the benzyl ester of D-serine was acylated with 875 mg (2.2 mmol) of acid (R) -3. -decanoyloxy-tetradecanoic, in the presence of 745 mg (2.5 mmol) of EDC-Mel in methylene chloride, to give 1.05 g (91%) of the benzyl ester of N - [(R) -3-decanoyloxytetradecanoyl] -D-serine , pf 51-52 ° C. NMR with 1H (CDCl 3) delta 0.88 (m, 6H), 1.1-1.7 (m, 34H), 2.30 (t, 2H, J = 7.7 Hz), 2.50 (m, 2H), 3.68 (s, 1H), 3.93 (d, 2H, J = 3.1 Hz), 4.62 (m, 1 H), 5.22 (m, 3H); 6.63 (d, 1 H, J = 6.9 Hz), 7.35 (broad s, 5H). (2) .- In the same manner as described in Example 2- (2), 1.0 g (2.02 mmol) of the compound prepared in Example 2- (1) was acylated with 884 mg (2.22 mmol) of acid ( R) -3-decanoyloxytetradecanoic, in the presence of 720 mg (2.4 mmol) of EDC-Mel and 100 mg of 4-pyrrolidinopyridine in methylene chloride, and then deprotected in 25 ml of aqueous AcOH to give 1.30 g (77%) 2- (Trimethylsilyl) ethyl-2-deoxy-3-0 - [(R) -3-decanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbonyl-amino) -β-D-glucopyranoside, as an amorphous solid . 1 H NMR (CDCl 3) delta 0.00 (s, 9H), 0.88 (m, 8H), 1.25 (m, 30H), 1.59 (m, 4H); 2.30 (t, 2H, J = 7.5 Hz), 2.52 (m, 2H), 3.42 (m, 1 H), 3.55 (m, 1 H), 3.66 (m, 1 H), 3.83 (dd, 1 H, J = 11.8, 4.6 Hz), 3.94 (m, 2H), 4.57 (d, 1 H, J = 8.2 Hz), 4.71 (m, 2H), 5.07 (m, 2H), 5.27 (d, 1 H, J = 8.8 Hz). (3) .- In the same manner as described in Example 2- (3), 1.25 g (1.50 mmol) of the compound prepared in (2) above was treated with 396 mg (1.65 mmol) of chloroformate 2, 2. , 2-trichloro-1,1-dimethyl and 0.15 ml (1.81 mmol) of pyridine in 25 ml of methylene chloride, followed by 0.42 ml (3.00 mmol) of triethylamine, 0.47 ml (2.25 mmol) of diphenyl chlorophosphate and 100 4-pyrrolidinopyridine mg, to give 1.31 g (69%) of 2- (trimethylsilyl) ethyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-decanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbo-nylamino) -β-D-glucopyranoside, as an amorphous solid.

NMR with 1H (CDCl 3) delta 0.0 (s, 9H), 0.89 (m, 8H), 1.1-1.7 (m, 34H), 1.82 (s, 3H), 1.90 (s, 3H), 2.30 (m, 4H) , 3.40 (c, 1 H, J = 9.6 Hz), 3.65 (m, 1 H), 3.89 (m, 1 H), 4.32 (m, 2H); 4.63 (m, 2H), 4.82 (d, 1 H, J = 12.1 Hz), 5.01 (d, 1 H, J = 8.2 Hz), 5.63 (m, 2H), 7.29 (m, 10H). (4) .- In the same manner as described in example 13- (4), 1.27 g (1.0 mmol) of the compound prepared in (3) above was deprotected with 5 ml of TFA, and then treated with the reagent from Vilsmeier, generated from 0.39 ml (5.0 mmol) of DMF and 0.22 ml (2.5 mmol) of oxalyl chloride, to give 1.06 g (89%) of 2-deoxy-4-0-diphenylphosphono-3- chloride 0 - [(R) -3-decanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethyloxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -alpha-D- glucopyranosyl, like a white foam.

NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.6 Hz), 1.1-1.55 (m, 34H); 1.78 (s, 3H), 1.88 (s, 3H), 2.18 (t, 2H, J = 7.7 Hz), 2.43 (m, 2H), 4.32 (m, 4H), 4.71 (m, 3H), 4.83 (m , 3H), 5.09 (m, 1 H), 5.50 (t, (1 H, J = 9.5 Hz), 5.77 (d, 1H, J = 8.0 Hz), 6.26 (d, 1 H, J = 3.4 Hz) 7.20 (m, 10H). (5) .- In the same manner as described in example 13- (5), 520 mg (0.90 mmol) and 1.0 g (0.84 mmol), respectively, of the compounds prepared in (1) and (4) were coupled. ) above, in the presence of 1.16 g (4.5 mmol) of AgOTf to produce 1.13 g (78%) of the benzyl ester of N - [(R) -3-decanoyloxytetradecanoyl] -0- [2-deoxy-4-0-diphenylphosphono] -3-0 - [(R) -3-decanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-di-methylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β -D-glucopyranosyl-D-serine.

NMR with 1H (CDCl 3) delta 0.88 (t, 12H, J = 6.6 Hz), 1.1-1.65 (m, 68H), 1.82 (s, 3H), 1.89 (s, 3H), 2.2-2.6 (m, 8H) , 3.40 (m, 1 H), 3.64 (m, 1 H), 4.01 (m, 2H), 4.27 (m, 2H), 4.44 (d, 1 H, J = 7.1 Hz), 4.60 (m, 2H) , 4.77 (m, 2H), 5.19 (m, 6H), 6.61 (d, H, J = 8.3 Hz), 7.05-7.45 (m, 15H). (6) .- In the same manner as described in Example 2- (7), 1.0 g (0.58 mmol) of the compound prepared in (5) above was deprotected with 1.9 g (29 mmol) of zinc and acylated with 280 mg (0.70 mmol) of (R) -3-decanoyloxytetra-decanoic acid, in the presence of 190 mg (0.77 mmol) of EEDQ, to yield 420 mg (44%) of the benzyl ester of N - [(R) -3 -decanoyl-oxytetradecanoyl] -0-deoxy-4-0-diphenylphosphono-2 - [(R) -3-decanoyl oxytetradecanoylamino] -3-0 - [(R) -3-decanoyloxytetradecanoyl] -β-D-glucopyranosyl] - D-serine, as an amorphous solid. (7) .- In the same manner as described in example 2- (8), 420 mg (0.25 mmol) of the compound prepared in (6) above, in the presence of palladium hydroxide on carbon, was hydrogenated in 10 ml. of EtOH and 400 mg of platinum oxide in 10: 1 EtOH / AcOH, to yield 118 mg (30%) of the triethylammonium salt of N - [(R) -3-decanoyloxytetradecanoyl] -0- [2-deoxy] -4-0-phosphono-2 - [(R) -3-decanoyloxytetradecanoylamino] -3-0 - [(R) -3-decanoyloxytetradecanoyl] -β-D-glucopyranosyl] -D-serine, as a white powder, mp 179-181 ° C.

IR (film) 3283, 3100, 2921, 2852, 1732, 1660, 1651, 1564, 1556, 1464, 1417, 1378, 1322, 1181, 1061, 856, 722 cm "1.

NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.8 Hz), 1.1-1.7 (m, 111 H), 2.2-2.7 (m, 12H), 3.06 (m, 6H), 3.33 (m , 5H), 3.78 (m, 2H), 3.95 (m, 2H), 4.22 (m, 1 H), 4.45 (d, 1 H, J = 7.5 Hz), 4.68 (broad s, 1 H), 5.13 ( m, 3H), 5.26 (m, 1 H).

NMR with 13 C (CDCl 3) delta delta 173.7, 173.5, 173.1, 171.1, 169.9, 100.3, 75.1, 73.9, 71.9, 71.1, 70.9, 70.2, 60.9, 53.9, 52.7, 46.0, 41.3, 40.8, 39.4, 34.6, 34.4, 31.9, 29.8, 29.7, 29.5, 29.4, 25.6, 25.4, 25.2, 25.1, 22.7, 14.1, 8.6.

Analysis calculated for C87H166N3O? 9P: C, 65.75; H, 10.53; N, 2.64; P, 1.95; Found: C, 65.32; H, 10.28; N, 2.53; P, 1.89.

EXAMPLE 16 (B15) PREPARATION OF THE TRIETILAMONIUM SALT OF N-HR1-3- PECANOILOXI-TETRAPECANOlL.-O-.2-PESOXI-4-O-PHOSPHONO-2 -. (R.-3-DECANOILOXI-TETRADECANOILAMINO1-3-Or (R) -3- PECANOYLOXITETRAPECANOILl-ß-d-GLUCOPYRANOSYL-L-SERINE (COMPOUND (I) R = R2 = R3 = n-CgH? GCO ?: X = Y = Q: ngm = P = q = 0: R4 = Rs = R7 = Rg = CO? H, Rfl = PO, H? (1) .- In the same manner as described in example 2- (5), 250 mg (1.08 mmol) of the benzyl ester of L-serine was acylated with 478 mg (1.2 mmol) of acid (R) -3. -decanoiloxite-tradecanoic, in the presence of 357 mg (1.2 mmol) of EDC-Mel in methylene chloride, to give 0.52 g (84%) of the benzyl ester of N - [(R) -3-heptanoyloxytetradecanoyl] -L-serine , pf 52-53 ° C.

NMR with 1H (CDCI3) delta 0.87 (t, 6H, J = 6.9 Hz), 1.1-1.7 (m, 34H), 2.29 (t, 2H, J = 7.5 Hz), 2.49 (d, 2H, J = 5.8 Hz ), 3.67 (s, 1 H), 3.97 (m, 2H), 4.63 (m, 1H), 5.19 (m, 3H), 6.61 (d, 1H, J = 7.1 Hz), 7.35 (broad s, 5H) . (2) .- In the same manner as described in example 13- (5), 500 mg (0.87 mmol) of the compound prepared in (1) above and 1.08 g (0.90 mmol) of the compound prepared in example 15 were coupled. - (4), in the presence of 1.16 g (4.5 mmol) of AgOTf, to give 1.35 g (89%) of the benzyl ester of N - [(R) -3-decanoyloxytetradecanoyl] -0- [2-deoxy-4-] 0-diphenylphosphono-3-0 - [(R) -3-decanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbo-nylamino) ) -beta-D-glucopyranosyl] -L-serine. NMR with 1H (CDCI3) delta 0.88 (t, 12H, J = 6.6 Hz), 1.0-1.65 (m, 68 H), 1.77 (s, 3H), 1.85 (s, 3H), 2.1-2.5 (m, 8H), 3.38 (c, 1H, J = 9.1 Hz), 3.65 (m, 1 H), 3.84 (m, 1 H), 4.27 (m, 3H), 4.70 (m, 5H), 4.84 (m, 4H), 5.14 (m, 3H), . 46 (t, 1H, J = 9.7 Hz), 6.07 (m, 1H), 6.62 (d, 1H, J = 8.0 Hz), 7.05-7.45 (m, 15H). (3) .- In the same manner as described in example 2- (7), 600 mg (0.34 mmol) of the compound prepared in (2) above was deprotected with 1.13 g (17.2 mmol) of zinc, and acylated with 150 mg (0.38 mmol) of (R) -3-decanoyloxytetrade-canoic acid, in the presence of 124 mg (0.50 mmol) of EEDQ, to give 362 mg (60%) of the benzyl ester of N - [(R) - 3-decanoyloxytetra-decanoyl] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-decanoyloxy-tetradecanoylamino] -3-0 - [(R) -. 3-decanoyloxytetradecanoyl] -β -D-glucopyranosyl] -L-serine, as an amorphous solid. (4) .- In the same manner as described in example 2- (8), 300 mg (0.17 mmol) of the compound prepared in (3) above was hydrogenated in the presence of 100 mg of palladium on carbon and 200 mg of platinum oxide, in 10: 1 THF / AcOH, to yield 120 mg (44%) of the triethylammonium salt of N - [(R) -3-decanoyloxytetradecanoyl] -0- [2-deoxy-4-0 -phosphono-2 - [(R) -3-decanoyloxytetradecanoylamino] -3-0 - [(R) -3-decanoyloxytetra-decanoyl] -β-D-glucopyranosyl] -L-serine, as a white powder, e.g. F. 175-176 ° C. IR (film) 3304, 2956, 2923, 2853, 1733, 1654, 1541, 1466, 1377, 1164, 1107, 1080, 845, 721 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.9 Hz), 1.1- 1.7 (m, 111 H), 2.2-2.75 (m, 12H), 3.07 (c, 6H, J = 7.2 Hz), 3.37 (m, 1 H), 3.5-3.95 (m , 8H), 4.21 (c, 1 H, J = 11.0 Hz), 4.54 (d, 1 H, J = 8.9 Hz), 4.61 (s broad, 1 H), 5.17 (m, 4H), 7.10 (d, 1H, J = 9.0 Hz), 7.43 (d, 1 H, J = 7.9 Hz). RMN with 3C (CDCI3) delta 176.3, 173.4, 173.2, 172.8, 172.0, 169.6, 169.2, 101.4, 74.7, 70.9, 69.3, 60.4, 53.2, 51.6, 46.1, 41.4, 41.0, 39.1, 34.2, 34.5, 34.3, 34.3, 34.2, 34.2, 34.1, 31.9, 29.8, 29.6, 29.6, 29.6, 29.4, 29.2, 29.2, 29.2, 29.2, 29.2, 29.2, 29.2, 29.2, 29.1, 8.6 for C87H? 66N3 ?? 9P.H20: C, 65.01; H, 10.54; N. 2.61; P, 1.93; Found: C, 64.92; H, 10.38; N, 2.58; P, 2.06.

EXAMPLE 17 (B16 PREPARATION PE SALT PE TRIETILAMONIO PE Nf (R.-3- NONANOILOXI-TETRAPECANOIL.-O-r2-PESOXI-4-O-PHOSPHONO-2-r (R) -3- NONANOILOXI-TETRAPECANOILAMINO1-3- Or (R.-3-NONANOYLOXlTETRAPECANOILl-ß-P-GLUCCOPIRANOSILl-L-SERINE (COMPOUND (I), RR? = Ra = n-CRH? 7CO, X = Y = Q; n = m = p = q = fl: R ^ = R, = R7 = R0 = H; Rfi = CO? H; RR = PO3H2 ,. (1) .- In the same manner as described in example 2- (5), 390 mg (2.0 mmol) of benzyl ester of L-serine was acylated with 780 mg (2.2 mmol) of acid (R) -3- nonanoyloxytetra-decanoic acid, in the presence of 845 mg (2.5 mmol) of EDC-Mel in methylene chloride, to give 1.0 g (89%) of the benzyl ester of N - [(R) -3-nonanoyloxytetradecanoyl] -L-serine, p. F. 52-53 ° C. NMR with 1H (CDCI3) delta 0.88 (t, 6H, J = 6.6 Hz), 1.1-1.7 (m, 32H), 2.30 (t, 2H, J = 7.7 Hz), 2.51 (d, 2H, J = 5.8 hz) ), 2.62 (t, 1 H, J = 6.0 Hz), 3.98 (m, 2H), 4.65 (m, 1 H), 5.19 (m, 3H), 6.58 (d, 1 H, J = 6.8 Hz), 7.35 (broad s, 5H). (2) .- In the same manner as described in Example 2- (2), 1.0 g (2.02 mmol) of the compound prepared in Example 2- (1) was acylated with 852 mg (2.22 mmol) of acid (R) -3-nonanoyloxytetradecanoic, in the presence of 720 mg (2.4 mmol) of EDC-Mel and 100 mg of 4-pyrrolidinopyridine in methylene chloride, and then deprotected in 25 ml of aqueous AcOH to give 1.31 g (79%) ) of 2- (trimethylsilyl) ethyl-2-deoxy-3-0 - [(R) -3-nonanoyloxytetradecanoyl] -2- (2,2,2-trichloroethoxycarbonyl-amino) -β-D-glucopyranoside, as a solid amorphous. NMR with 1H (CDCl 3) delta 0.00 (s, 9H), 0.88 (m, 8H), 1.25 (m, 28H), 1.59 (m, 4H), 2.30 (t, 2H, J = 7.5 Hz), 2.52 (m , 2H), 3.42 (mn, 1 H); 3.55 (m, 1 H), 3.66 (m, 1 H), 3.83 (dd, 1 H, J = 11.8, 4.6 Hz), 3.94 (m, 2H); 4.57 (d, 1 H, J = 8.2 Hz), 4.71 (m, 2H), 5.07 (m, 2H), 5.27 (d, 1 H, J = 8.8 Hz). (3) .- In the same manner as described in Example 2- (3), 1.25 g (1.52 mmol) of the compound prepared in (2) above was treated with 400 mg (1.67 mmol) of chloroformate 2, 2. , 2-trichloro-1,1-dimethylethyl and 0.15 ml (1.84 mmol) of pyridine in 25 ml of methylene chloride, followed by 0.42 ml (3.04 mmol) of triethylamine, 0.47 ml (2.28 mmol) of diphenyl chlorophosphate and 100 4-pyrrolidinopyridine mg, to yield 1.30 g (67%) of 2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-nonanoyloxytetradecanoyl] -6-0- (2,2,2- trichloro-1, 1-dimethylethoxycarbonyl) -2- (2,2,2-trichloro-ethoxycarbonylamino) -β-D-glucopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.0 (s, 9H), 0.88 (m, 8H), 1.1-1.7 (m, 32H), 1.82 (s, 3H), 1.89 (s, 3H), 2.22 (m, 6H) , 3.33 (m, 1 H), 3.53 (m, 1 H), 3.80 (m, 1 H), 3.96 (m, 1 H), 4.31 (m, 2 H), 4.55 (m, 2 H), 4.83 (d , 1 H, J = 12.0 Hz), 5.01 (d, 1H, J = 7.9 Hz), 5.62 (m, 1 H), 7.28 (m, 10H). (4) .- In the same way as described in example 13- (4), 1.26 g (1.0 mmol) of the compound prepared in (3) above was deprotected with 5 ml of TFA and then treated with the Vilsmeier reagent, generated from 0.39 ml (5.0 mmol) of DMF and 0.22 ml ( 2.5 mmol) of oxalyl chloride, to give 1.07 g (91%) of 2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-nonanoyloxytetradecanoyl] -6-0- (2, 2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -alpha-D-glucopyranosyl, as a white foam. NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.9 Hz), 1.25-1.55 (m, 32H), 1.78 (s, 3H), 1.88 (s, 3H), 2.18 t, 2H, J = 7.7 Hz), 2.43 (m, 2H), 4.34 (m, 4H), 4.70 (m, 3H), 4.83 (m, 3H), 5.09 (m, 1 H), 5.51 (t, 1 H, J = 10.2 Hz), 5.78 (d, 1 H, J = 8.0 Hz), 6.25 (d, 1 H, J = 3.6 Hz), 7.19 (m, 10H). (5) .- In the same manner as described in example 13 (5), 505 mg (0.90 mmol) and 1.0 g (0.85 mmol), respectively, of the compounds prepared in (1) and (4) were coupled. above, in the presence of 1.16 g (4.5 mmol) of AgOTf, to yield 1.03 g (71%) of the benzyl ester of N - [(R) -3-nonanoyloxytetradecanoyl] -0- [2-deoxy-4-0-diphenylphosphono] -3-0 - [(R) -3-nonanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-di-methylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β -D-glucopyranosyl] -L-serine, 1 H NMR (CDCl 3) delta 0.88 (t, 12H, J = 6.9 Hz), 1.0-1.65 (m, 64H), 1.78 (s, 3H), 1.82 (s, 3H) ), 2.1-2.5 (m, 8H), 3.38 (m, 1 H), 3.64 (m, 1 H), 3.83 (m, 1 H), 4.25 (m, 3H), 4.73 (m, 5H), 5.18 (m, 5H), 6.07 (m, 1 H), 6.60 (d, 1H, J = 7.8 Hz), 7.05-7.45 (m, 15H). (6) .- In the same way as described in the example 2- (7), 1.0 g (0.59 mmol) of the compound prepared in (5) above was deprotected with 1.93 g (29.5 mmol) of zinc, and acylated with 273 mg (0.71 mmol) of acid (R) -3- nonanoilox itetrade-canoic in the presence of 195 mg (0.78 mmol) of EEDQ, to give 405 mg (42%) of the benzyl ester of N - [(R) -3-nonanoyloxytetra-decanoyl] -0- [deoxy-4-0- diphenylphosphono-2 - [(R) -3-nonanoyloxyte-tradecanoylamino] -3-0 - [(R) -3-nonanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L-serine, as an amorphous solid. (7) .- In the same manner as described in example 2- (8), 405 mg (0.25 mmol) of the compound prepared in (6) above was hydrogenated, in the presence of palladium hydroxide on carbon in 10 ml of EtOH and 400 mg platinum oxide in 10: 1 EtOH / AcOH, to give 185 mg (48%) of the triethylammonium salt of N - [(R) -3-nonanoyloxytetradecanoyl] -0- [2- Deoxy-4-0-phosphono-2 - [(R) -3-nonanoyloxytetradecanoylamino] -3-0 - [(R) -3-non-nanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L-serine, as a powder white, mp 177-179 ° C. IR (film) 3306, 2955, 2923, 2853, 1732, 1660, 1538, 1467, 1378, 1252, 1165, 1106, 1080, 960, 844, 722 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 ( t, 18H, J = 6.8 Hz), 1.1- 1.7 (m, 105H), 2.2-2.75 (m, 12H), 3.07 (c, 6H, J = 7.1 Hz), 3.2-3.5 (m, 5H), 3.85 (m, 4H), 4.23 (d, 1 H, 10.2 Hz), 4.51 (d, 1H, J = 8.0 Hz), 4.64 (broad s, 1 H), 5.18 (m, 4H). 13 C NMR (CDCI3 ) delta 173.3, 172.8, 172.2, 169.6, 169.1, 101.5, 74.8, 70.9, 70.8, 69.3, 60.5, 53.2, 51.5, 46.1, 41.5, 41.0, 39.2, 34.5, 34.3, 34.1, 32.0, 31.9, 29.8, 29.6, 29.4, 29.3, 25.6, 25.2, 25.1, 22.7, 14.1, 8.7 Analysis calculated for CwH-idoNsOigP: C, 65.21; H, 10.42; N, 2.72; P, 2.00; Found: C, 65.48; H, 10.32; N, 2.62; P, 2.12.

EXAMPLE 18 (B17) PREPARATION PE SALT PE TRIETILAMINO PE N -. (4) -3-OCTANOILOXI- TETRAPECANOlL1-O-r2-PESOXI-4-O-PHOSPHONO-2-r (R.-3-OCTANOILOXI-TETRAPECANOILAMINO1- 3-Or (R -3-OCTANOILOXITETRAPECANOIL1-ß- P-GLUCOPIRANOSILM-SERINE (COMPOUND (I), R = R? = Ra = n-C7H? SCO, X = Y = O; n = m = p = q = 0; R4 = R ^ R7 = R "= H; R6 = CO2H, R« (1) .- In the same manner as described in example 2- (5), 390 mg (2.0 mmol) of the benzyl ester of L-serine was acylated with 815 mg (2.2 mmol) of acid (R) -3. -octanoyloxytetradecanoic in the presence of 745 mg (2.5 mmol) of EDC-Mel in methylene chloride, to yield 1.02 g (93%) of the benzyl ester of N - [(R) -3-octanoyloxytetradecanoyl] -L-serine, p. F. 50-51 ° C. NMR with 1H (CDCI3) delta 0.88 (t, 6H, J = 6.8 Hz), 1.1-1.7 (m, 30H), 2.30 (t, 2H, J = 7.7 Hz), 2.51 (d, 2H, J = 5.8 Hz ), 2.60 (t, 1 H, J = 6.0 Hz), 3.97 (m, 2H); 4.65 (m, 1H), 5.22 (m, 3H), 6.61 (d, 1H, J = 6.9 Hz), 7.35 (broad s, 5H). (2) .- In the same manner as described in Example 2- (2), 1.0 g (2.02 mmol) of the compound prepared in Example 2- (1) was acylated with 821 mg (2.22 mmol) of the acid ( R) -3-octanoi loxitetradecanoic, in the presence of 720 mg (2.4 mmol) of EDC-Mel and 100 mg of 4-pyrrolidinopyridine in methylene chloride; then it was deprotected in 25 ml of 90% aqueous AcOH to yield 1.35 g (83%) of 2- (trimethylsilyl) ethyl-2-deoxy-3-0 - [(R) -3-octanoyloxytetradecanoyl] -2- ( 2,2,2-trichloro-ethoxycarbonylamino) -β-D-glucopyranoside, as an amorphous solid.

NMR with 1H (CDCl 3) delta 0.00 (s 9H), 0.88 (m, 8H), 1.25 (m, 25H), 1.60 (m, 4H), 2.30 (t, 2H, J = 7.5 Hz), 2.53 (m, 2H), 3.42 (m, 1 H), 3.52 (m, 1 H), 3.66 (m, 1 H), 3.83 (dd, 1 H, J = 11.8, 4.4 Hz), 3.94 (m, 2H), 4.56 (d, 1 H, J = 8.3 Hz), 4.64 (d, 1 H, J = 11.8 Hz) , 4.77 (d 1 H, J = 11.8 Hz), 5.08 (m, 2H), 5.30 (broad s, 1 H). (3) .- In the same manner as described in Example 2- (3), 1.30 g (1.61 mmol) of the compound prepared in (2) above was treated, with 425 mg (1.77 mmol) of chloroformate of 2, 2,2-trichloro-1,1-dimethylethyl and 0.16 ml (1.95 mmol) of pyridine in 25 ml of methylene chloride, followed by 0.45 ml (3.22 mmol) of triethylamine, 0.50 ml (2.42 mmol) of diphenyl chlorophosphate and 100 mg of 4-pyrrolidinopyridine, to yield 1.42 g (71%) of 2- (trimethylsilyl) ethyl-2-deoxy-4-0_diphenylphosphono-3-0 - [(R) -3-octanoyl-oxytetradecanoyl] -6 -0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2) 2-trichloroethoxycarbonylamino) - beta-D-glucopyranoside, as an amorphous solid.

NMR with 1H (CDCl 3) delta 0.0 (s, 9H), 0.88 (m, 8H), 1.1-1.7 (m, 30H), 1.82 (s, 3H), 1.89 (s, 3H), 2.23 (m, 6H) , 3.37 (m, 1 H), 3.65 (m, 1 H), 3.83 (m, 1 H), 3.96 (m, 1 H), 4.55 (m, 2H), 4.83 (d, 1 H, J = 11.8 Hz), 5.01 (d, 1 H, J = 8.2 Hz), 5.20 (m, 1 H); 7.29 (m, 10H). (4) .- In the same manner as described in example 13- (4), 1.24 g (1.0 mmol) of the compound prepared in (3) above was deprotected with 5 ml of TFA and then treated with the reagent Vilsmeier, generated from 0.39 ml (5.0 mmol) of DMF and 0.22 ml (2.5 mmol) of oxalyl chloride, to give 1.0 g (87%) of 2-deoxy-4-0-diphenylphosphono-3-0 chloride - [(R) -3-octanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -alpha-D-glucopyranosyl , like a white foam.

NMR with 1H (CDC! 3) delta 0.88 (t, 6H, J = 6.7 Hz), 1.25-1.55 (m, 30H), 1.78 (s, 3H), 1.88 (s, 3H), 2.18 (t, 2H, J = 7.7 Hz), 2.43 (m, 2H), 4.29 (m, 4H), 4.72 (m, 3H), 5.09 (m, 1H), 5.51 (t, 1 H, J = 9.9 Hz), 5.79 (d , 1 H, J = 7.9 Hz), 6.25 (d, 1 H, J = 3.5 Hz), 7.29 (m, 10H). (5) .- In the same manner as described in Example 13- (5), 490 mg (0.90 mmol) and 1.0 g (0.86 mmol), respectively, of the compounds prepared in (1) and (4) were coupled. above, in the presence of 1.16 g (4.5 mmol) of AgOTf, to give 0.99 g (69%) of the benzyl ester of N - [(R) -3-octanoyloxytetradecanoyl] -0- [2-deoxy-4-0-diphenylphosphono] -3-0 - [(R) -3-octanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethyloxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β -D-glucopyranosyl] -L-serine.

NMR with 1H (CDCl 3) delta 0.88 (t, 12H, J = 6.9 Hz), 1.0-1.65 (m, 60H), 1.77 (s, 3H), 1.85 (s, 3H), 2.1-2.5 (m, 8H) , 3.37 (m, 1 H), 3.65 (m, 1 H), 3.83 (m, 1 H), 4.27 (m, 3 H), 4.72 (m, 5 H), 5.18 (m, 4 H); 5.46 (t, 1 H, J = 9.8 Hz), 6.06 (m, 1 H); 6.60 (d, 1 H, J = 8.0 Hz), 7.06-7.45 (m, 15H). (6) .- In the same manner as described in Example 2- (7), 0.95 g (0.57 mmol) of the compound prepared in (5) above was deprotected with 1.86 g (28.5 mmol) of zinc and acylated with 252 mg (0.68 mmol) of (R) -3-octanoyloxytetradecaneic acid in the presence of 185 mg (0.75 mmol) of EEDQ, to give 433 mg (47%) of the benzyl ester of N - [(R) -3- octanoyloxytetra-decanoyl] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-octanoyloxy-tetradecanoyl] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R ) -3-octano-ioxytetradecanoylamino] -3-0 - [(R) -3-octanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L-serine, as an amorphous solid. (7) .- In the same manner as described in example 2- (8), 433 mg (0.27 mmol) of the compound prepared in (6) above was hydrogenated, in the presence of 250 mg of palladium hydroxide on carbon in 10%. ml of EtOH and 400 mg of platinum oxide in 10: 1 EtOH / AcOH to give 196 mg (48%) of the triethylammonium salt of N - [(R) -3-octanoyloxytetradecanoyl] -0- [2-deoxy] -4-0-phosphono-2 - [(R) -3-octanoyloxytetradecanoylamino] -3-0 - [(R) -3-octanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L-serine, as a white powder, . F. 177-178 ° C. IR (film) 3296, 2956, 2923, 2853, 1732, 1645, 1546, 1466, 1378, 1315, 1170, 1082, 1056, 961, 846, 722 crn. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 ( t, 18H, J = 6.6 Hz), 1.1- 1.7 (m, 99H), 2.2-2.75 (m, 12H), 3.08 (c, 6H, J = 7.1 Hz), 3.39 (d, 1 H, J = 8.8 Hz), 3.6-4.0 (m, 8H), 4.22 (c, 1 H, 10.3 Hz), 4.53 (d, 1 H, J = 8.2 Hz), 4.63 (m, 1 H), 5.18 (m, 4H) , 7.04 (d, 1 H, J = 8.8 Hz), 7.42 (d, 1 H, J = 8.0 Hz).

NMR with 13C (CDCI3) delta 176.8, 173.3, 173.2, 172.7, 172.2, 169.6, 169.1, 101.5, 74.8, 70.9, 70.8, 69.3, 60.5, 53.2, 51.5, 46.2, 41.5, 41.1, 39.2, 34.5, 34.3, 34.1 , 34.0, 32.0, 31.8, 29.8, 29.6, 29.4, 29.3, 29.2, 29.1, 25.6, 25.3, 25.2, 25.0, 22.7, 14.1, 8.7. Analysis calculated for C8? Hi54N3 ?? gP.H 0: C, 63.87; H, 10.32; N, 2.76; P, 2.03; Found: C, 63.96; H, 10.29; N, 2.69; P, 1.67.

EXAMPLE 19 (B18 PREPARATION PE SALT PE TRIOTYLAMIDE PE NKRi-3-HEPTANOILOXI-TETRAPECANOIL1-O-r2-PESOXI-4-O-PHOSPHONO-2-r (R.-3- HEPTANOILOXI-TETRAPECANOILAMlNO.-3-Qr (R .-3- HEPTANOILOXITETRAPECANOIL.-ß-d-GLUCOPIRANOSILl-L-SERINA.

(COMPOUND (I) Ri = R? = Ra = nC «H .aCO: X = Y = O: ngm = p = q = 0: Ri = s = R7 = Rg = H; Rfi = CO? H, R «= POaH?) (1) .- In the same manner as described in Example 2- (5), 390 mg (2.0 mmol) of the benzyl ester of L-serine was acylated with 780 mg (2.2 mmol) of (R) -3 acid. -heptanoyloxy-tetadecanoic in the presence of 745 mg (2.5 mmol) of EDC-Mel in methylene chloride, to give 0.97 g (91%) of the benzyl ester of N - [(R) -3-heptanoyloxytetradecanoyl] -L-serine; p.f. 46-48 ° C. NMR with 1H (CDCI3) delta 0.88 (t, 6H, J = 6.9 Hz), 1.1-1.7 (m, 28H), 2.30 (t, 2H, J = 7.7 Hz), 2.50 (d, 2H, J = 5.8 Hz ), 2.62 (t, 1 H, J = 6.0 Hz), 3.97 (m, 2H), 4.65 (m, 1 H), 5.19 (m, 3H), 6.61 (d, 1 H, J = 6.9 Hz), 7.35 (broad s, 5H). (2) .- In the same manner as described in Example 2- (2), 1.0 g (2.02 mmol) of the compound prepared in Example 2- (1) was acylated with 790 mg (2.22 mmol) of the acid ( R) -3-heptanoyloxytetradecanoic in the presence of 720 mg (2.4 mmol) of EDC-Mel and 100 mg of 4-pyrrolidinopyridine in methylene chloride, and then deprotected in 25 ml of 90% aqueous AcOH to yield 1.30 g (81%). %) of 2- (trimethylsilyl) ethyl-2-deoxy-3-0 - [(R) -3-heptanoyloxytetradecanoyl] -2- (2,2,2-trichloro-ethoxycarbonylamino) -β-D-glucopyranoside, as a amorphous solid.

NMR with 1H (CDCl 3) delta 0.00 (s, 9H), 0.88 (m, 8H), 1.25 (m, 24H), 1.59 (m, 4H), 2.30 (t, 2H, J = 7.5 Hz), 2.52 (m, 2H), 3.42 (m, 1 H), 3.55 (m, 1 H), 3.66 (m, 1 H), 3.83 (dd, 1 H, J = 11.5, 4.2 Hz), 3.94 (m, 2H), 4.57 (d, 1H, J = 8.3 Hz), 4.64 (d, 1H, J = 12.1 Hz), 4.76 (d, 1 H, J = 11.9 Hz), 5.09 (m, 2H), 5.31 (d, 1 H, J = 8.7 Hz). (3) .- In the same manner as described in Example 2- (3), 1.25 g (1.58 mmol) of the compound prepared in (2) above was treated with 417 mg (1.74 mmol) of chloroformate of 2.2, 2-trichloro-1,1-dimethylethyl and 0.15 ml (1.91 mmol) of pyridine in 25 ml of methylene chloride, followed by 0.44 ml (3.16 mmol) of triethylamine, 0.49 ml (2.37 mmol) of diphenyl chlorophosphate and 100 mg of 4-pyrrolidino-pyridine, to yield 1.34 g (69%) of 2- (trimethylsilyl) ethyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-heptanoyloxytetradecane-yl] -6 -0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-tri-chloroethoxycarbonylamino) -β-D-glucopyranoside, as an amorphous solid.

NMR with 1H (CDCl 3) delta 0.0 (s, 9H), 0.88 (m, 8H), 1.1-1.7 (m, 28H), 1.82 (s, 3H), 1.89 (s, 3H), 2.35 (m, 4H) , 3.37 (m, 1 H), 3.61 (m, 1 H), 3.80 (m, 1 H), 4.32 (m, 2H), 4.63 (m, 2H), 4.83 (d, 1 H, J = 12.0 Hz ), 5.01 (d, 1 H, J = 8.2 Hz), 5.62 (m, 2H); 7.29 (m, 10H). (4) .- In the same manner as described in example 13- (4), 1.23 g (1.0 mmol) of the compound prepared in (3) above was deprotected with 5 ml of TFA and then treated with the reagent Vilsmeier, generated from 0.39 ml (5.0 mmol) of DMF and 0.22 ml (2.5 mmol) of oxalyl chloride, to give 1.0 g (87%) of 2-deoxy-4-diphenylphosphono-3-0 chloride - [(R) -3-heptanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -alpha-D-glucopyranosyl , like a white foam.

NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.9 Hz), 1.25-1.55 (m, 28H), 1.78 (s, 3H), 1.88 (s, 3H), 2.18 (t, 2H, J = 7.6 Hz), 2.43 (m, 2H), 4.26 (m, 4H), 4.73 (m, 3H), 5.09 (m, 1 H), 5.51 (t, 1 H, J = 10.2 Hz), 5.77 (d, 1 H; J = 8.0 Hz), 6.25 (d, 1 H, J = 3.3 Hz), 7.19 (m, 10 H). (5) .- In the same manner as described in example 13- (5), 480 mg (0.90 mmol) and 0.98 g (0.86 mmol), respectively, of the compounds prepared in (1) and (4) were coupled. ) above, in the presence of 1.16 g (4.5 mmol) of AgOTf, to give 1.06 g (75%) of the benzyl ester of N - [(R) -3-heptanoyloxytetradecanoyl] -0- [2-deoxy-4-0- diphenylphosphono-3-0 - [(R) -3- heptanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dime-toxicarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) - β-D-glucopyranosyl] -L-serine. 1 H NMR (CDCl 3) delta 0.88 (m, 12 H), 1.0-1.65 (m, 56 H), 1.77 (s, 3 H), 1.85 (s, 3 H), 2.1-2.5 (m, 8 H), 3.38 (m, 1 H), 3.64 (m, 1 H), 3.83 (m, 1 H), 4.25 (m, 3 H), 4.78 (m, 5 H), 5.16 (m, 4 H), 5.46 (t, 1 H, J = 9.9 Hz), 6.06 (m, 1H), 6.60 (d, 1H, J = 7.7 Hz), 7.06-7.45 (m, 15H). (6) .- In the same manner as described in Example 2- (7), 1.0 g (0.61 mmol) of the compound prepared in (5) above was deprotected with 2.0 g (30.5 mmol) of zinc and acylated with 260 mg (0.73 mmol) of (R) -3-heptanoyloxytetra-decanoic acid in the presence of 200 mg (0.80 mmol) of EEDQ, to give 440 mg (45%) of the benzyl ester of N - [(R) -3- heptanoyloxytetra-decanoyl] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-heptanoyloxy-tetradecanoylamino] -3-0 - [(R) -3-heptanoyloxytetradecanoyl] -β-D- glucopyranosyl] -L-serine, as an amorphous solid. (7) .- In the same manner as described in Example 2- (8), 440 mg (0.28 mmol) of the compound prepared in (6) above was hydrogenated in the presence of 250 mg of palladium hydroxide on carbon in 10 ml of EtOH and 400 mg of platinum oxide in 10: 1 EtOH / AcOH, to give 208 mg (51%) of the triethylammonium salt of N - [(R) -3-heptanoyloxytetradecanoyl] -0- [2 -deoxy-4-0-phosphono-2 - [(R) -3-heptanoyloxytetradecanoylamino] -3-0 - [(R) -3-heptanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L-serine, as a white powder , pf 176-177 ° C.

IR (film) 3307, 2956, 2924, 2854, 1732, 1650, 1545, 1466, 1378, 1316, 1170, 1080, 956, 841, 722 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (m, 18H), 1.1-1.7 (m, 93H), 2.2-2.75 (m, 12H), 3.08 (c, 6H, J = 7.2 Hz), 3.40 (d, 1 H, J = 10.2 Hz), 3.6-4.0 ( m, 7H), 4.24 (m, 2H), 4.52 (d, 1 H, J = 8.0 Hz), 4.63 (m, 1 H), 5.19 (m, 4H), 7.04 (d, 1 H, J = 8.6 Hz), 7.40 (d, 1 H, J = 8.4 Hz). NMR with 13 C (CDCI3) delta 177.1, 173.2, 173.1, 172.7, 172.3, 169.5, 168.9, 101.5, 75.0, 74.8, 71.2, 70.9, 69.1, 60.5 , 53.1, 51.4, 46.1, 41.5, 41.0, 39.2, 34.5, 34.3, 34.3, 34.1, 34.2, 34.2, 34.0, 31.2, 31.6, 31.5, 29.5, 29.6, 29.4, 29.0, 28.9, 28.8, 25.6, 25.3, 25.2, 25.2, 22.7, 22.6 , 14.1, 8.7 Analysis calculated for C78Hu8N3? 19P: C, 64.04; H, 10.20; N, 2.87; P, 2.12; Found: C, 63.77; H, 10.11; N, 2.85; P. 2.02.

EXAMPLE 20 (B19) PREPARATION PE SALT PE TRIETILAMONIO PE 2 -. (R.-3- TETRAPECANO-1LOX1TETRAPECANOILAMINO1ETIL-2-PESOXI-4-O-PHOSPHONO-3-Or (R -3-TETRAPECANOILOXITETRAPECANOIL1-2-r (R ) -3- TETRAPECANOILOXITETRA-PECANOILAMINOI-ß-P- g O: ngmgpgqg 0; Ri g Rs = RR = R? G Rg g H: R «POaH? .. (1) .- 330 mg (1.1 mmol) of 2-amino-1- (tert-butyldiphenylsilyloxy) ethane and 500 mg (1.1 mmol) of (R) -3-tetradecanoxytetradecanoic acid in 10 ml of methylene chloride were dissolved and treated with 500 mg of molecular sieves in powder of 4Á. After one hour 297 mg (1.2 mmol) of EEDQ was added and the reaction was stirred for 18 hours, filtered through Celite® and concentrated in vacuo. The residue was chromatographed on silica gel using 15% EtOAc / hexanes to give 675 mg (92%) of a colorless solid. A 500 mg portion (0.68 mmol) of this material was deprotected with 1 ml (1 mmol) of 1 M TBAF in THF, in 5 ml of THF, stirring at room temperature for 2 hours. The reaction mixture was diluted with 50 ml of ether and washed with 2 x 50 ml of brine. The brine was again extracted with 2 x 50 ml of ether and the combined organic extracts were dried over sodium sulfate and concentrated in vacuo to give 338 mg (62%) of 2 - [(R) -3-tetradecanoyloxytetradecanoylamino] ethanol, as a white off-white solid. (2) .- In the same manner as described in Example 2- (6), 338 mg (0.68 mmol) of the compound prepared in (1) above and 786 mg (0.61 mmol) of the compound prepared in the example were capped. 2- (4), in the presence of 770 mg (3.05 mmol) of mercuric cyanide to give 245 mg (24%) of 2 - [(R) -3-tetradecanoyloxytetradecanoylamino] ethyl-2-deoxy-4-0-diphenyl- phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonyl) - β-D-glucopyranoside, as an amorphous solid.

NMR with H (CDCI3) delta 0.88 (t, 12H, J = 6.9 Hz), 1.1-1.8 (m, 84H), 1.81 (s, 3H), 1.89 (s, 3H), 2.15-2.55 (m, 8H); 3.25 (m, 1 H), 3.47 (m, 2H), 3.67 (m, 1 H), 3.83 (m, 2H), 4.28 (dd, 1 H, J = 12.2, 4.9 Hz), 4.36 (d, 1 H, J = 11.0 Hz), 4.68 (m, 2H), 4.78 (d, 1 H, J = 11.6 Hz), 4.94 (d, 1 H, J = 11.6 Hz), 5.16 (m, 2H), 5.53 ( t, 1 H, J = 10.0 Hz), 6.06 (d, 1H, J = 4.9 Hz), 5.19 (m, 1 H), 7.25 (m, 10H). (3) .- In the same manner as described in Example 2- (7), 500 mg (0.29 mmol) of the compound prepared in (2) above was deprotected with 980 mg (15 mmol) of zinc and then acylated with 155 mg (0.34 mmol) of (R) -3-tetradecanoyloxy-tetradecanoic acid, in the presence of 110 mg (0.44 mmol) of EEDQ, to give 315 mg (62%) of 2 - [(R) -3-tetradecanoyloxytetradecanoyl) -amino] ethyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-tetradecane-iloxytetradecanoyl] -2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -β-D-glucopyranoside , as an amorphous solid. (4) .- In the same manner as described in example 2- (8), 200 mg (0.113 mmol) of the compound prepared in (3) above was hydrogenated, in the presence of 100 mg of platinum oxide, to give 142 mg (76%) of the triethylammonium salt of 2 - [(R) -3-tetradecanoyloxytetradecanoylamino] ethyl-2-deoxy-4-0-phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -β-D-glucopyranoside, as a white solid; p. F. 175-176 ° C. IR (film) 3285, 3098, 2955, 2919, 1731, 1659, 1642, 1556, 1468, 1379, 1250, 1228, 1174, 1110, 1083, 1046, 962, 857 cm. "1 NMR with 1H (CDCI3-CD3OD ) delta 0.88 (t, 18H, J = 6.0 Hz), 1.1- 1.7 (m, 135H), 2.2-2.7 (m, 15H), 3.06 (c, 6H, J = 7.1 Hz), 3.2-4.1 (m, 8H), 4.21 (c, 1 H, J = 9.9 Hz), 4.51 (d, 1 H, J = 8.2 Hz), 5.05-5.25 (m, 4H), 7.33 (d, 1 H, J = 8.5 Hz) 7.50 (broad 1H, J = 4.8 Hz). NMR with 13C (CDCI3) delta 173.7, 173.3, 170.6, 170.3, 169.9, 100.9, 75.8, 73.0, 71.3, 71.1, 70.9, 70.6, 68.3, 60.6, 55.1, 45.7, 41.6, 41.2, 39.5, 34.6, 34.5, 34.4, 32.0, 29.8, 29.4, 29.3, 25.4, 25.4, 25.1, 22.7, 14.2, 8.6 Analysis calculated for C ßH190N3 7 7P.2H2:: C, 67.28; H, 11.18; N, 2.40; P, 1.77; Found: C, 67.01; H, 11.18; N. 2.15; P. 2.01.

EXAMPLE 21 (B20 PREPARATION PE SALT PE TRIETILAMONIO PE 2-HR.-3- PECANOILOXI-TETRAPECANOILAMINO1-ETIL-2-PESOXI-4-O-PHOSPHONO- 3-Or (R) -3-PECANOILOXITETRAPECANOIL1-2-r (R ) -3- PECANOYLOXITETRAPECANOIL-AMINOI-ß-P-GLUCOPIRANOSIPA (COMPOUND (I), R1 = R2 g Ra = n-CgH? GCO: X = Y = O; n = m = p = q = 0: R = Rs - RR = R7 s Rg = H; Rn = PO3H2) - (1) .- In the same manner as described in example 20 (1), 450 mg (1.5 mmol) of 2-amino-1- (tert-butyldiphenylsiloxy) ethane was acylated with 600 mg (1.5 mmol) of acid (R ) -3-decanoyloxytetradecanoic, in the presence of 594 mg (2.0 mmol) of EDC-Mel and then deprotected with 2.56 ml (2.5 mmol) of 1.0 M TBAF in THF, in 10 ml of THF to give 488 mg (81%) 2 - [(R) -3-decanoyloxytetradecanoylaminohetanol, as a matt white solid. (2) .- In the same manner as described in example 13- (5), 385 g (0.87 mmol) of the compound prepared in (1) above and 1.05 g (0.87 mmol) of the compound prepared in the example were coupled. 15- (4), in the presence of 560 mg (2.2 mmol) of AgOTf, to give 1.04 g (74%) of 2 - [(R) -3-decanoyloxytetradecanoylamino] ethyl-2-deoxy-4-0-diphenylphosphono- 3-0 - [(R) -3-decanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D- glucopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.88 (t, 12H, J 0 6.9 Hz), 1.1-1.6 (m, 68H), 1.78 (s, 3H9, 1.88 (s, 3H), 2.18 (t, 2H, J = 7.7 Hz), 2.44 (m, 2H), 4.34 (m, 5H), 4.72 (m, 2H), 4.83 (c, 1 H, J = 9.3 Hz), 5.09 (m, 1 H), 5.51 (t, 1 H, J = 10.2 Hz), 5.79 (d, 1 H, J = 8.0 Hz), 6.26 (d, 1 H, J = 3.4 Hz), 7.31 (m, 10H). (3) .- In the same way which was described in Example 2- (7), 700 mg (0.44 mmol) of the compound prepared in (2) above was deprotected with 1.42 g (21.7 mmol) of zinc, and then acylated with 190 mg (0.48 mmol) of (R) -3-decanoyloxytetradecanoic acid, in the presence of 148 mg (0.6 mmol) of EEDQ, to give 432 mg (62%) of 2 - [(R) -3decanoyloxytetradecanoyl-amino] ethyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-decanoyl-oxytetradecanoyl] -2 - [(R) -3-decanoyloxytetradecanoylamino] -β-D-glucopyranoside, as an amorphous solid. (4) .- In the same manner as described in example 2- (8), 400 mg (0.25 mmol) of the compound prepared in (3) above was hydrogenated, in the presence of 200 mg of platinum oxide, to give 200 mg (52%) of the triethylammonium salt of 2 - [(R) -3-decanoyloxytetradecanoylamino] ethyl-2-deoxy-4-0-phosphono-3-0 - [(R) -3-decanoyloxytetradecanoyl] - 2 - [(R) -3-decanoyloxytetra-decanoylamino] -β-glucopyranoside, as a white solid; p. F. 165-166 ° C. IR (film) 3289, 3094, 2956, 2922, 2853, 1732, 1658, 1644, 1556, 1467, 1379, 1247, 1164, 1107, 1081, 1048 cm "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (t , 18H, J = 6.9 Hz), 1.1- 1.7 (m, 111 H), 2.2-2.7 (m, 15H), 3.05 (c, 6H, J = 7.1 Hz), 3.2-3.85 (m, 9H), 4.52 (d, 1H, J = 8.2 Hz), 5.05-5.25 (m, 4H), 7.21 (d, 1H, J = 8.5 Hz), 7.42 (broad t, 1 H).

NMR with 13 C (CDCl 3) delta 173.8, 173.3, 170.7, 170.3, 170.0, 100.9, 75.6, 73.0, 71.3, 70.9, 70.6, 68.3, 60.7, 55.0, 45.8, 41, 6, 41.2, 39.5, 34.5, 34.4, 34.1 , 31.9, 29.8, 29.6, 29.5, 29.4, 25.4, 25.1, 22.7, 14.2, 8.6. Analysis calculated for C86Hi66N3 ?? 7P.H20: C, 66.08; H, 10.83; N, 2.69; P, 1.98; Found: C, 65.80; H, 10.63; N, 2.63; P, 2.04.

EXAMPLE 22 (B21) PREPARATION PE SALT PE TRIETILAMONIO PE 3-HR.-3- TETRAPECA-NOILAMINO1PROPIL-2-PESOXI-4-O-PHOSPHONO-3-OR (R.-3- TETRAPEANANYLOXITETRAPECANOIL1-2-r (R) -3-TETRAPECANOILOXI- TETRAPECANOILAMINO1) -ß-P-GLUCOPIRANOSIPA. (COMPOSED (I ..

Ri g R? g Ra g n-C .aHr.CO: X = Y = Q: n = 1; m = p = q = 0: Ri = R! i = Rii = R7 = Rq H; Re = POaH2). (1) .- In the same manner as described in Example 20- (1), 470 mg (1.5 mmol) of 3-amino-1- (tert-butyldiphenylsilyloxy) propane was acylated with 680 mg (1.5 mmol) of acid (R) -3-tetradecanoyloxytetradecanoic, in the presence of 595 mg (2.0 mmol) of EDC-Mel, and then deprotected with 2.0 ml, (2.0 mmol) of 1.0 M TBAF in THF, in 10 ml of THF, to give 698 mg (91%) of 3 - [(R) -3-tetradecanoyloxytetradecanoylamino] -1-pro-panol, as a white off-white solid. (2) .- In the same manner as described in Example 13- (4) 7.9 g (5.88 mmol) of the compound prepared in Example 2- (3) was deprotected with 10 ml of TFA and then treated with the Vilsmeier reagent, generated from 1.8 ml (23.5 mmol) of DMF and 1.03 ml (11.76 mmol) of oxalyl chloride in 60 ml of methylene chloride, to give 6.32 g (85%) of 2-deoxychloride 4-0-diphenylphosphono-3-0 - [(R) -3-tetradecanoyloxytetrade-canoil] -6-0- (2,2,2-trichloro-1-1, dimethylethoxycarbonyl) -2- (2,2,2 -trichloroethoxycarbonylamino) -alpha-D-glucopyranosyl, as a white foam. NMR with 1H (CDCl 3) delta 0.88 (t, 6H, J = 6.8 Hz), 1.2-1.55 (m, 42H), 1.78 (s, 3H), 1.88 (s, 3H), 2.18 (t, 2H, J = 7.5 Hz), 2.43 (m, 2H), 4.31 (m, 4H); 4.68 (d, 1 H, J = 11.9 Hz), 4.74 (d, 1 H, J = 11.9 Hz), 4.83 (c, 1 H, J = 9.3 Hz), 5.09 (m, 1 H), 5.51 (t, 1 H, J = 9.7 Hz), 5.78 (d, 1 H, J = 8.0 Hz), 6.26 (d, 1H, J = 3.4 Hz), 7.31 (m, 10H). (3) .- In the same manner as described in example 13- (5), 613 mg (1.2 mmol) of the compound prepared in (1) above and 1.5 g (1.2 mmol) of the compound prepared in (2) were coupled. ) above, in the presence of 642 mg (2.5 mmol) of AgOTf, to give 1.43 g (68%) of 3 - [(R) -3-tetradecanoyloxytetra-decanoylamino] propyl-2-deoxy-4-0-diphenylphosphono-3 -0 - [(R) -3-tetradecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethyl-ethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D -gluco-pyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.88 (t, 12H, J = 6.9 Hz), 1.1-1.8 (m, 86H), 1.82 (s, 3H), 1.89 (s, 3H), 2.20 (t, 2H, J = 7.6 Hz), 2.29 (t, 2H, J = 7.7 Hz), 2.44 (m, 4H), 3.21 (m, 1 H), 3.42 (m, 1 H), 3.54 (m, 2H), 3.80 (m, 1 H), 3.94 (m, 1 H), 4.28 (dd, 1 H, J = 12.3, 5.2 Hz), 4.38 (d, 1 H, J = 10.8 Hz), 4.70 (m, 3H), 4.81 (d , 1 H, J = 8.2 Hz), 5.14 (m, 2H); 5.47 (t, 1 H, J = 9.6 Hz), 6.13 (d, 1 H, J = 7.6 Hz), 6.22 (broad s, 1 H); 7.25 (m, 10H). (4) .- In the same manner as described in Example 2- (7), 700 mg (0.40 mmol) of the compound prepared in (3) above was deprotected with 1.32 g (20.1 mmol) of zinc, and then acylated with 200 mg (0.44 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid, in the presence of 125 mg (0.5 mmol) of EEDQ, to give 435 mg (60%) of 3 - [(R) -3 -tetradecanoyloxytetradecanoylamino] propyl-2-deoxy-4-0-diphenyl-phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -2 - [(R) -3-tetradecanoyloxytetradecanoylamino]) - β-D-glucopyranoside, as an amorphous solid. (5) .- In the same manner as described in example 2- (8), 400 mg (0.22 mmol) of the compound prepared in (4) above was hydrogenated in the presence of 200 mg of platinum oxide to give 170 mg (45%) of the triethylammonium salt of 3 - [(R) -3-tetradecanoyloxytetradecanoylamino] propyl-2-deoxy-4-0-phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl} -2 - [(R) -3-tetradecanoyloxytetradecanoylamino]) - ß-D-glucopyranoside, as a white solid, p. F. 171-172 ° C.

IR (film) 3288, 3094, 2955, 2919, 2850, 1731, 1658, 1344, 1556, 1468, 1378, 1320, 1251, 1226, 1172, 1106, 1083, 1044 cm "1.

NMR with H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.0 Hz), 1.1-1.7 (m, 135H), 2.2-2.7 (m, 15H), 3.06 (c, 6H, J = 7.1 Hz) , 3.2-4.1 (m, 8H), 4.21 (c, 1 H, J = 9.9 Hz), 4.51 (d, 1 H, J = 8.3 Hz), 5.05-5.25 (m, 4H), 7.23 (t, 1 H, J = 5.3 Hz), 7.33 (d, 1 H, J = 8.6 Hz). NMR with 13 C (CDCl 3) delta 173.5, 173.4, 170.6, 170.2, 169.9, 100. 6, 75.8, 71.5, 70.9, 70.5, 66.8, 60.4, 55.3, 45.6, 41.4, 39.4, 36.3, 34.6, 34.5, 34.2, 31.9, 29.7, 29.4, 29.4, 29.3, 29.3, 29.2, 25.4, 25.1, 22.7, 14.1, 8.5. Analysis calculated for C99H? 92N3O? P.H20: C, 67.42; H, 11.20; N, 2.38; P, 1.76; Found: C, 66.97; H, 11.01; N, 2.38; P, 1.95.

EXAMPLE 23 (B22) PREPARATION PE SALT PE TRIETHYLMONIUM PE 4-HR) -3- TETRAPECANOILOXITETRAPECANOILAMINO1BUTIL-2-PESOXI-4-O-PHOSPHONO-3-O -. (R.-3-TETRAPECANOILOXITETRAPECANOIL1-2-r (R. -3- TETRA-PECANOYLOXITETRAPECANOILAMINO1-β-P-GLUCOPYRANOSIPA (COMPOUND (0. R g R = Ra = nC.aH27CO: X = Y g O: ng 2: mp = q = 0; R = Rs = RR = R? G Rg = H: RR g POaH?,. (1) .- In the same manner as described in Example 20 (1), 500 mg (1.53 mmol) of 4-amino-1- (tert-butyldiphenylsilyloxy) butane was acylated with 695 mg (1.53 mmol) of acid (R ) -3-tetradecanoyloxytetradecanoic, in the presence of 595 mg (2.0 mmol) of EDC-Mel, and then deprotected with 2.5 ml (2.5 mmol) of 1.0 M TBAF in THF, in 15 ml of THF, to give 651 mg (81 %) of 4 - [(R) -3-tetradecanoyloxytetradecanoylamino] -1-butanol, as a white, off-white solid. (2) .- In the same manner as described in example 13- (5), 650 mg (1.25 mmol) of the compound prepared in (1) above and 1.6 g (1.25 mmol) of the compound prepared in the example were coupled. 22- (2), in the presence of 1.16 g (4.5 mmol) of AgOTf to give 1.65 g (75%) of 4 - [(R) -3-tetradecanoyloxytetradecanoylamino] butyl-2-deoxy-4-0-diphenyl-phosphono -3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] 6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbo-nylamino) -β- D-glucopyranoside, as an amorphous solid.

NMR with 1H (CDCl 3) delta 0.88 (t, 12H, J = 6.9 Hz), 1.1-1.8 (m, 88H), 1.82 (s, 3H), 1.89 (s, 3H), 2.15-2.55 (m, 8H), 3.24 (m, 2H), 3.50 (m, 2H), 3. 83 (m, 2H), 4.27 (dd, 1 H, J = 12.1, 3.8 Hz), 4.32 (d, 1 H, J = 11.5 Hz), 4.66 (m, 2H); 4.78 (d, 1 H, J = 12.1 Hz), 4.89 (d, 1 H, J = 8.0 Hz), 5.15 (m, 2H), 5.54 (t, 1 H, J = 9.7 Hz), 5.95 (m, 2H), 7.25 (m, 10H). (3) .- In the same manner as described in Example 2- (7), 700 mg (0.39 mmol) of the compound prepared in (2) above was deprotected with 1.30 g (19.8 mmol) of zinc, and then was acylated with 195 mg (0.43 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid, in the presence of 124 mg (0.5 mmol) of EEDQ, to give 421 mg (60%) of 4 - [(R) -3-tetradecanoyloxytetradecanoylamino ] butyl-2-deoxy-4-0-diphenyl-phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -2 - [(R) -3-tetradecanoyloxytetradecanoylamino]) - ß-D-glucopyranoside, as a amorphous solid. (4) .- In the same manner as described in Example 2- (8), 400 mg (0.22 mmol) of the compound prepared in (3) above was hydrogenated in the presence of 200 mg of platinum oxide to give 212 mg (55%) of the triethylammonium salt of 4 - [(R) -3-tetradecanoyloxytetradecanoylamino] butyl-2-deoxy-4-0-phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -2- [(R) -3-tetradecanoyloxytetradecanoylamino] -β-D-glucopyranoside, as a white solid; p.f. 171-172 ° C. IR (film) 328, 2955, 2920, 2851, 1732, 1645, 1550, 1467, 1378, 1181, 1107, 1083, 1044, 721 cm. "1 NMR with 1H (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.9 Hz), 1.1-1.7 (m, 135H), 2.2-2.7 (m , 19H), 3.05 (c, 6H, J = 7.1 Hz), 3.18 (m, 2H), 3.3-3.5 (m, 6H), 3.78 (m, 3H), 3.97 (d, 1 H, J = 12.5 Hz ), 4.23 (c, 1 H, J = 10.0 Hz), 4.50 (d, 1 H, J = 8.5 Hz), 5.13 (m, 4H), 7.12 (d, 1H, J = 9.1 Hz). (CDCI3) delta 173.9, 173.4, 173.3, 170.8, 169.9, 169.8, 101.0, 75.6, 73.2, 71.4, 71.1, 70.6, 68.9, 60.7, 54.8, 45.9, 41.5, 39.6, 38.9, 34.6, 34.3, 32.0, 29.8, 29.5, 29.0, 28.9, 26.3, 25.4, 25.1, 22.7, 14.2, 8.7 Analysis calculated for C? OoH? G4N3 ?? 7P.H20: C, 68.26; H, 11.23; N, 2.39; P, 1.76; Found: C , 68.21; H, 11.03; N, 2.26; P, 1.73.

EXAMPLE 24 (B23) PREPARATION PE SALT PE TRIETILAMONIO PE 4-HR.-3- TETRAPECANOILOXITETRAPECANOILAMINO1-HEXIL-2-PESOXI-4-O-PHOSPHONO-3-Or (R) -3-TETRAPECANOILOXITETRAPECANOIL1-2-r (R.-3- TETRAPECANOILOXlTETRAPECANOILAMINOI- ß-P-GLUCOPYRANOSIPA (COMPOUND (I) R g R? g Ra = nC.aH? 7CO: X = YO: n 4; mgpqg 0: Ri Rs = RR = R7 = Rg = H: R «g POaH ?) (1) .- In the same manner as described in Example 20- (1), 1.48 g (4.15 mmol) of 6-amino-1- (tert-butyldiphenylsilyloxy) hexane was acylated with 2.07 g (4.56 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid, in the presence of 1.35 g (4.65 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid, in the presence of 1.35 g (4.56 mmol) of EDC-Mel, and then deprotected with 1.53 ml ( 1.53 mmol) of 1.0 M TBAF in THF, in 46 ml of THF, to give 700 mg (30%) of 6 - [(R) -3-tetradecanoyloxy-tetradecanoylamino] -1-hexanol, as a white off-white solid. (2) .- In the same manner as described in example 13- (5), 689 mg (1.20 mmol) of the compound prepared in (1) above, and 1.25 g (1.00 mmol) of the compound prepared in the Example 22- (2), in the presence of 1.28 g (5.0 mmol) of AgOTf, to give 1.59 g (94%) of 4 - [(R) -3-tetradecanoyloxytetradecanoylamino] hexyl-2-deoxy-4-0-diphenyl -phosphon-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbo-nylamino) -β-D-glucopyranoside, as an amorphous solid. NMR with 1H (CDCl 3) delta 0.88 (t, 12H, J = 6.6 Hz), 1.1-1.8 (m, 92H), 1.82 (s, 3H), 1.89 (s, 3H), 2.22 (t, 2H, J = 7.6 Hz), 2.29 (t, 2H, J = 7.4 Hz), 2.45 (m, 4H), 3.22 (m, 1 H), 3.46 (m, 2H), 3.83 (m, 2H), 3.94 (m, 1 H), 4.31 (m, 2H), 4.64 (m, 2H), 4.83 (d, 1H, J = 12.1 Hz), 4.97 (d, 1H, J = 7.8 Hz), 5.17 (m, 2H); 5.59 (t, 1 H, J = 8.8 Hz), 5.75 (m, 1H), 5.84 (d, 1H, J = 7.6 Hz), 7.25 (m, 10H). (3) .- In the same manner as described in Example 2- (7), 1.57 g (0.88 mmol) of the compound prepared in (2) above was deprotected with 2.88 g (44.1 mmol) of zinc, and then Acylated with 481 mg (1.06 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid, in the presence of 327 mg (1.32 mmol) of EEDQ, to give 1.57 g (97%) of 4 - [(R) -3-tetradecanoyloxytetradecanoylamino] hexyl-2-deoxy-4-0-diphenyl-phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -2 - [(R) -3-te-tradecanoylo-tetradecanoylamino]) - β-D-glucopyranoside, as an amorphous solid. (4) .- In the same manner as described in Example 2- (8), 1.57 g (0.85 mmol) of the compound prepared in (3) above was hydrogenated, in the presence of 157 mg of platinum oxide, to give 130 mg (10% of the triethylammonium salt of 4 - [(R) -3-tetradecanoyloxytetradecanoylamino] hexyl-2-deoxy-4-0-phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -2- [(R) -3-te-tradecanoyloxytetradecanoylamino] -β-D-glucopyranoside, as a white solid, mp 150-152 ° C.

IR (film) 3284, 3099, 2954, 2920, 2851, 1731, 1657, 1637, 1557, 1467, 1418, 1378, 1320, 1249, 1179, 1108, 1083, 1044, 856, 721 cm "1. NMR with? (CDCI3-CD3OD) delta 0.89 (t, 18H, J = 6.6 Hz), 1.1-1.7 (m, 135H), 2.2-2.7 (m, 23H), 3.05 (c, 6H, J = 7.1 Hz), 3.18 ( m, 2H), 3.39 (d, 1H, J = 8.2 Hz), 3.49 (c, 1H, J = 7.5 Hz), 3.82 (m, 2H), 3.99 (d, 1H, J = 11.9 Hz), 4.25 ( c, 1H, J = 8.9 Hz), 4.59 (m, 2H), 5.18 (m, 4H), NMR with 13C (CDCI3) delta 173.7, 173.3, 170.6, 169.7, 169.4, 100.6, 75.5, 73.1, 71.3, 70.9 , 70.6, 69.2, 60.6, 55.2, 45.8, 41.7, 41.4, 39.5, 39.4, 34.6, 34.3, 34.2, 34.2, 34.2, 34.2, 34.9, 29.2, 29.2, 29.2, 29.2, 29.2, 22.5, 25.2, 22.7, 14.1, 8.6. calculated for C? o2H? 98N3O? P.H20: C, 68.53; H, 11.28; N, 2.33; P, 1.73; Found: C, 68.63; H, 11.12; N, 2.26; P, 1.66; EXAMPLE 25 (B24) PREPARATION PE SALT PE TRIETILAMONIO PE N-KR.-3- TETRAPECA-NOILOXITETRAPECANOIL1-O-PHOSPHONO-2-r (R? -3- TETRAPECANOILOXITETRA-PECANOILAMINQ1-3-0-r (R.-3- TETRAPECANOILOXITETRAPECANOILI-ß- P-GLUCOPYRANOSYLI-L- SERINAMIPA. (COMPOUND (I) .R = R? = Ra = nC? AH27CO; X = Y = O: n = m = p. = q =; 0; t = R, = R7 = Rg = CONH2; Ra = POaH. (1) .- A suspension of 0.157 g (1.18 mmol) of L-serinamide hydrochloride and 0.61 g (1.34 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid in 6 ml of methylene chloride was treated., with 0.18 ml (1.3 mmol) of triethylamine, and the resulting solution was stirred with 4Á molecular sieves, for 30 minutes. Then 0.437 g (1.77 mmol) of EEDQ was added and the mixture was stirred for 16 hours at room temperature. The product that precipitated was collected and washed with 2 x 25 ml of methylene chloride, to give 0.455 g (71%) of N - [(R) -3-tetradecanoyloxytetradecanoyl] -L-serinamide, as a colorless powder, m.p. 126-130 ° C.

NMR with? (CDCI3) delta 0.88 (t, 6H, J = about 7 Hz), 1.15-1.7 (m, 42H), 2.31 (t, 2H, J = 7.5 Hz), 2.51 (d, 2H, J = 6.3 Hz) 3.56 (s broad, 1 H); 3.65 (dd, 1 H, J = 11.2, 5.5 Hz), 3.86 (dd, 1 H, J = 11.2, 4.5 Hz), 4.21 (s 2 H), 4.40 (m, 1 H), 5.22 (m, 1 H) ). (2) .- In the same manner as described in Example 2- (6), 0.23 g (0.246 mmol) of the compound prepared in (1) above and 0.961 g (0.745 mmol) of the compound prepared in the example were coupled. 2- (4), in the presence of 0.43 g (1.7 mmol) of mercuric cyanide, to give 0.527 g (71%) of N - [(R) -3-tetra-decanoyloxytetradecanoyl] -0- [2-deoxy-4] -0-diphenylphosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranosyl] -L-serinamide, as an amorphous solid. NMR with? (CDCb) delta 0.88 (t, 12H, J = about 7 H), 1.0-1.7 (m, 84H), 1.80 and 1.89 (2s, 6H), 2.21 (t, 2H, J = 7.5 Hz), 2.30 ( t, 2H, J = 7.5 Hz), 2.37 (m, 2H), 2.47 (m, 2H), 3.54 (m, 1 H), 3.68 (dd, 1H, J = 8, J = 11 Hz), 3.86 ( d wide, 1 H, J = 11 Hz), 4.16 (dd, 1 H, J = 11.4 Hz), 4.24 (d, 1 H, J = 12, 4.3 Hz), 4.40 (d, 1 H, J = 12 Hz), 4.6-4.8 (m, 4H), 5.00 (d, 1 H, J = 8 Hz), 5.1-5.25 (m, 2H), 5.4-5.55 (m, 2H), 5.84 (s broad, 1 H ), 6.61 (broad s, 2H), 7.1-7.35 (m, 10H). (3) .- In the same manner as described in Example 2- (7), 0.44 g (0.254 mmol) of the compound prepared in (2) above was deprotected, with 0.83 g (13 mmol) of zinc, and Then it was acylated with 0.14 g (0.31 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid, in the presence of 0.095 g (0.38 mmol) of EEDQ, to give 0.271 g (59%) of N - [(R) -3- tetradecanoyloxytetradecanoyl] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -3-0 - [(R) -3-tetra-decanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L-Serinamide, as an amorphous solid.

NMR with? (CDCI3) delta 0.88 (t, 18H, J = 6.5 Hz), 1.0-1.7 (m, 126 H), 2.03 (broad s, 1 H), 2.15-2.55 (m, 12H), 3.5-4.05 (m, 5H), 4.14 (dd, 1 H, J = 10, 3.5 Hz), 4.5-4.65 (m, 2H), 4.68 (d, 1 H, J = 8.1 Hz), 5.05-5.25 (m, 3H), 5.31 (t, 1 H, J = around 10 Hz), 5.58 (broad s, 1 H), 6.31 (d, 1 H, J = 8 Hz), 6.85-6.95 (m, 2H), 7.1-7.4 (m , 10H). (4) .- In the same manner as described in example 2- (8), 0.25 g (0.14 mmol) of the compound prepared in (3) above was hydrogenated, in the presence of 0.125 g of platinum oxide, to give 0.195 g (80%) of the triethylammonium salt of N - [(R) -3-tetradecanoyloxytetradecanoyl] -0- [2-deoxy-4-0-phosphono-2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -3 -0 - [(R) -3-tetradecanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L-serine-mide, as a colorless solid, mp 190-191 ° C. (with decomposition). IR (film) 3293, 2921, 2850, 1732, 1717, 1651, 1636, 1557, 1540, 1458, 1165, 1033 cm "1. NMR with α (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 7 Hz ), 1.0- 1.7 (m, 135 H), 2.2-2.7 (m, 12H), 3.05 (c, 6H, J = 7.2 Hz), 3.2-3.45 (m), 3.5-4.15 (m, 5H), 4.21 (c, 1H, J = around 10 Hz), 4.53 (d, 1 H, J = 8.1 Hz), 4.58 (m, 1 H), 5.0-5.3 (m, 4H), 7.25 (d, 1 H, J = 8.4 Hz), 7.40 (d, 1 H, J = 7.2 Hz). NMR with 13C (CDCI3-CD3OD) delta 173.7, 173.5, 172.5, 170.7, 170. 5, 170.4, 101.4, 75.5, 73.4, 71.1, 70.9, 70.2, 68.6, 60.9, 53.9, 52.2, 45.6, 41.2, 41.0, 38.9, 34.4, 34.2, 31.8, 29.6, 29.5, 29.3, 29.1, 25.2, 24.9, 22.6, 14.0, 8.3.

Analysis calculated for C99H? 9-? N4O? SP-2.5 H20: C, 66.00; H, 10.97; N, 3.11; P, 1.72; Found: C, 66.04; H, 10.99; N, 3.03; P. 1.95.

EXAMPLE 26 (B25) PREPARATION PE SALT PE TRIOTYLAMIDE PE Nf (R) -3- PECANOYLOXI-TETRAPECANOIL1-O-r2-PESOXY-4-O-PHOSPHONO-2-r (R) -3- PECANOYLOXITETRAPECANOILAMINOl-3-Or ( R.-3- PECANOYLOXITETRA-PECANOILI-ß-P-GLUCOPYRANOSYLI-L-SERINAMIPA (COMPOUND (I), R = R? = Ra = n-CgHiaCO; X = Y = O: n = mgpgqg 0: R4 g Rs = R7 = Rg = H; Rfi g CONH ?: R «s POaH (1) .- In the same manner as described in example 25- (1), 169 mg (1.2 mmol) of L-serinamide hydrochloride was acylated, with 478 mg (1.2 mmol) of acid (R) -3- decanoyloxytetradecanoic, in the presence of 371 mg (1.5 mmol) of EEDQ in methylene chloride, to yield 428 mg (74%) of N- [(R) -3-decanoyloxytetradecanoyl] -L-serinamide, as a white solid. NMR with 1H (CDCl 3) delta 0.88 (t, 6H), 1.1-1.7 (m, 34H), 2.33 (t, 2H, J = 7.5 Hz), 2.54 (d, 2H, J = 6.6 Hz), 3.35 (s) , 2H), 3.72 (dd, 1 H, J = 11.0, 5.2 Hz), 3.84 (dd, 1 H, J = 11.3, 5.0 Hz), 4.20 (t, 1 H, J = 5.1 Hz), 5.26 (t , 1 H, J = 6.4 Hz). (2) .- In the same manner as described in example 13- (5), 410 mg (0.85 mmol) of the compound prepared in (1) above and 1.05 g (0.87 mmol) of the compound prepared in the example were coupled. 15- (4), in the presence of 560 mg (2.2 mmol) of AgOTf to yield 780 g (56%) of N - [(R) -3-decanoyloxytetradecanoyl] -0- [2-deoxy-4-0-diphenylphosphono] -3-0 - [(R) -3-decanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D -glucopyranosyl] -L-serinamide, as an amorphous solid. NMR with? (CDCI3) delta 0.88 (t, 12H), 1.1-1.6 (m, 68H), 1.80 (s, 3H), 1.89 (s, 3H), 2.30 (m, 8H), 3.53 (m, 1 H), 3.68 (m, 1 H), 3.85 (broad d, 1 H, J = 9.4 Hz), 4.15 (dd, 1 H, J = 10.8, 3.7 Hz), 4.24 (d, 1 H, J = 12.3, 4.6 Hz), 4.40 (d, 1 H, J = 10.8) , 4.64 (m, 4H), 5.00 (d, 1 H, J = 8.2 Hz), 5.18 (m, 2H), . 46 (m, 2H), 5.83 (m, 1 H), 6.60 (m, 2H), 7.30 (m, 10H). (3) .- In the same manner as described in Example 2- (7), 600 mg (0.36 mmol) of the compound prepared in (2) above, with 1.19 g (18.2 mmol) of zinc, was deprotected and acylated with 160 mg (0.4 mmol) of (R) -3-decanoyloxytetradecanoic acid, in the presence of 124 mg (0.50 mmol) of EEDQ to produce 371 mg (62%) of N - [(R) -3-decanoyloxytetra-decanoyl] -0- [2-deoxy-4-0-diphenylphosphono-2 - [(R) -3-decanoyloxy-tetradecanoylamino] -3-o - [(R) -3-decanoyloxytetradecanoyl] -β-D-glucopyranosyl] -L -serinamide, as an amorphous solid. (4) .- In the same manner as described in Example 2- (8), 330 mg (0.20 mmol) of the compound prepared in (3) above, in the presence of 200 mg of platinum oxide, was hydrogenated to produce 120 mg (44%) of the triethylammonium salt of N - [(R) -3-decanoyloxytetradecanoyl] -0- [2-deoxy-4-0- phosphono-2 - [(R) -3-decanoyloxytetradecanoylamino] -3 -0 - [(R) -3-decanoyloxy-tetradecanoyl] -β-D-glucopyranosyl] -L-serinamide, as a white powder, e.g. F. 187-189 ° C. IR (film) 3419, 3286, 3220, 3098, 2955, 2922, 2852, 1732, 1680, 1662, 1644, 1559, 1467,1247,1167,1107, 1080, 1051, 965, 913 cm "1. NMR with? (CDCI3-CD3OD) delta 0.89 (t, 18H, J = 7.9 Hz), 1.1- 1.7 (m, 111H), 2.2-2.7 (m, 12H), 3.07 (c, 6H, J = 7.1 Hz), 3.68 ( m, 1H), 3.87 (m, 1H), 4.09 (dd, 1H, J = 10.8, 3.6 Hz), 4.22 (m, 1H), 4.53 (d, 1H, H = 8.2 Hz), 4. 58 (m, 1H), 5.13 (m, 3H), 5.28 (m, 1H9, 7.53 (d, 1H, J = 9.0 Hz), 7.56 (d, 1H, J = 7.7 Hz). NMR with 13C (CDCI3) delta 173.5, 173.2, 170.2, 169.8, 102.3, 75.7, 73.5, 71.3, 70.7, 70.1, 68.8, 60.8, 53.9, 51.7.45.8, 41.5, 41.1, 39.1, 34.6, 34.5, 34.2, 32.0, 29.7, 29.6 , 29.5, 29.4, 25.7, 25.4, 25.1, 22.7, 14.1, 8.6 Analysis calculated for C87H-? 6N4O? 8P.H20: C, 65.05; H, 10.60; N, 3.49; P, 1.93; Found: C, 65.06; H, 10.40; N.3.31; P, 2.00.

EXAMPLE 27 (B26 PREPARATION PE SALT PE TRIETILAMONIO PEL ESTER METÍLICO PE Nr (R.-3-TETRAPECANOILOXlTETRAPECANOIL.-O-r2-PESOXI-4-O-PHOSPHONO-2 -. (R) -3-TETRADECANOILOX ?? TRADECANOILAMINQ1 -3-O -. (R) -3-TETRA-DECANOYLOXITETRADECANOILl-ß-D-GLUCOPYRANOSYL1-L-SERINE (COMPOUND (I) .R = R? = Ra = n-CraH27CO.X = Y = O: n = mgp = qg 0: R? = Rs = R7 = Rg = H: Rfi g CQ2Me, Ra = POaH?. (1) .- A solution of 0.290 g (0.157 mmol) of the compound prepared in Example 12- (2) in 20 ml of THF was hydrogenated in the presence of 50 mg of palladium on charcoal at 5%, at room temperature and at atmospheric pressure, for 3 hours. The catalyst was removed by filtration and the filtrate was concentrated. A solution of the residue in 5 ml of chloroform was treated 0 ° C, with a solution of 0.5 mmol of diazomethane in 5 ml of ether, and then stirred for 30 minutes at 0 ° C. 0.5 ml of AcOH was added and the resulting colorless solution was diluted with 50 ml of ether, washed with 25 ml of saturated aqueous sodium bicarbonate, dried over sodium sulfate and concentrated. Rapid chromatography on silica gel (gradient elution: -25% EtOAc-hexanes) yielded 0.199 g (72%) of the N - [(R) -3-tetradecanoyloxytetradeca-noyl] -0-2-deoxy-4-0-diphenylphosphono-3-0- methyl ester [(R) -3-tetradecanoyloxy-tetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranosyl] -L-Serine, as an amorphous solid.

NMR with? (CDCI3) delta 0.88 (t, 12H; J = about 6.5 Hz), 1. 1-1.75 (m, 84 H), 1.81 and 1.89 (2s, 6H), 2.36 (t, 2H, J = 7.5 Hz), 2.25-2.6 (m, 6H), 3.48 (c, 1 H, J = 8 Hz), 3.7-3.9 (m, 5H), 4.2-4.4 (m, 3H), 4.6-4.85 (m, 4H), .88 (d, 1 H) , J = 7.8 Hz), 5.03-5.22 (m, 2H), 5.49 (t, 1 H, J = about 9.5 Hz), 6.21 (broad s, 1 H), 6.59 (d, 1 H, J = 7.8 Hz), 7.1-7.4 (m, 10H). (2) .- In the same manner as described in Example 2- (7) 0.195 g (0.111 mmol) of the compound prepared in (1) above was deprotected with 0.36 g (5.5 mmol) of zinc, and acylated with 0.060 g (0.13 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid, in the presence of 0.0451 g (0.17 mmol) of EEDQ to give 0.138 g (69%) of the N - [(R) methyl ester. -3-tetradecanoyloxytetradecanoyl] -0 - [(R) -4-0-diphenylphosphono -2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -3-0 - [(R) -3-tetra-decanoyloxytetradecanoyl-β-D- glucopyranosyl] -L-serine, as an amorphous solid. NMR with? (CDCI3) delta 0.88 (t, 18H, J = about 6.5 Hz), 1.0-1.75 (m, 126 H), 2.15-2.45 (m, 10H), 2.52 (dd, 1 H; J = 14.7, 6 Hz), 2.66 (dd, 1 H, J = 14.7, 6 Hz), 3.35 (broad s, 1 H), 3.4-3.8 (m, 7H), 3.88 (dd, 1 H, J = 11 Hz), 4.18 (dd, 1 H, J = 11 Hz), 4.6-4.75 (m, 2H9, 5.03 (d, 1 H, J = 7.8 Hz), 5.1-5.25 (m, 3H), 5.50 (t , 1 H, J = about 9.5 Hz), 6.50 (d, 1 H, J = 7.2 Hz), 6.97 (d, 1H, J = 7.8 Hz), 7.1-7.4 (m, 10H). (3). - In the same manner as described in Example 2- (8), 0.100 g (0.055 mmol) of the compound prepared in (2) above was hydrogenated, in the presence of 50 mg of platinum oxide, to give 0.055 g (57 %) of the triethylammonium salt of N - [(R) -3-tetradecanoyloxytetradecanoyl] -0- [2-esoxy-4-0-phosphono-2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -3- methyl ester 0- { (R) -3-tetradeanoyloxytetradecanoyl] -beta-D-glucopyranosyl] -L-serine, as a colorless solid, mp 142-143 ° C (with decomposition). IR (film) 3289, 2955, 2921 , 2852, 1733, 1718, 1699, 1652, 1558, 1540, 1521, 1506, 1469, 1457, 1360, 1259 cm "1. NMR with α (CDCI3-CD3OD) delta 0.88 (t, 18H, J = 6.5. Hz), 1.0- 1.7 (m, 135 H), 2.2-2.7 (m, 12H), 3.05 (c, 6H), J = 7.5 Hz), 3.31 (d, 1 H, J = 9.3 Hz), 3.37 (s, 1 H), 3.55-3.9 (m, 10H), 3.97 (d, 1 H, J = 12 Hz), 4.1-4.25 (m, 2H), 4.55-4.65 (m, 2H) , 5.05-5.25 (m, 3H), 7.23 (d, 1 H, J = 8 Hz), 7.47 (d, 1 H, J = 7. 2 Hz). NMR with 13C (CDCI3) delta 173.6, 173.4, 170.5, 170.4, 170.1, 100.7, 75.9, 72.8, 71.2, 70.8, 70.6, 68.5, 60.3, 55.3, 52.7, 52.4, 47.7, 41, 5, 40.9, 39.7, 34.6 , 34.5, 34.3, 32.0, 29.8, 29.4, 25.4, 25.1, 22.7, 14.2, 8.5. Analysis calculated for C? OoH? G2N3O? GP.H20: C, 67.11; H, 10.93; N, 2.35; P, 1.73; Found: C, 66.91; H, 10.93; N. 2.31; P, 2.11.

EXAMPLE 28 (B27) PREPARATION OF N- (CARBOXYMETHYL-N-α (R) -3-TETRADECANOILOXITETRADECANOIL1-2-AMINOETIL-2- DESOXI-4-o-PHOSPHONO-2-r (R) -3- TETRADECANOILOXITETRADECANOILAMINO1-3 -O-. (R.-3- TETRADECANOILOXITETRADECANOILI-ß-GLUCOPIRANOSIDA.

(COMPOUND (i), R = R? = Ra = n-C? AH? 7CO: X = Y = Q: n = m = p = 0: R? = Rs = Rfi = Rg = H: R7 = CO? H ?: q = 1: Ra = POaH2). (1) .- In the same manner as described in Example 2- (5), 0.25 g (1.43 mmol) of the N- (2-hydroxyethyl) glycine terbutyl ester was acylated with 0.714 g (1.57 mmol) of the acid (R) -3-tetradecanoyloxytetradecanoic, in the presence of 0.466 g (1.57 mmol) of EDC-Mel, to give 0.46 g (51%) of the terbutyl ester of N- (2-hydroxyethyl) -N - [(R) -3 -tetradecanoiloxitetra-decanoil] -glycine, as an amorphous solid. NMR with (CDCI3) delta 0.88 (t, 6H, J = about 6.5 Hz), 1.15-1.7 (m, 51 H), 2.26 (t, 2H, J = 7.5 Hz), 2.60 (dd, 1H, J = 6.5 15 Hz), 2.86 (dd, 1 H, J = 6.7, 15 Hz), 3.40-4.15 (m, 7H), 5.25 (m, 1 H). (2) .- In the same manner as described in 13- (5), 0.21 g (0.334 mmol) of the compound prepared in (1) above and 0.458 g (0.368 mmol) of the compound prepared in Example 22- were coupled. (2), in the presence of 0.688 g (268 mmol) of AgOTf, to give 0.39 g (64%) of N- (t-butyloxycarbonylmethyl) -N- [(R) -3-tetradecanoyloxytetradecanoyl] -2-aminoethyl-2 -deoxy-4-0-diphenyl-phosphono-3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2, 2,2-trichloroethoxycarbo-nylamino) -β-D-glucopyranoside, as an amorphous solid. NMR with (CDCI3) delta 0.88 (t, 12H; J = about 6.5 Hz), 1.0-1.95 (m, 99H), 2.1-2.6 (m, 7H), 2.84 (dd, 1 H, J = 5, 15 Hz), 3.2-4.15 (m, 8H), 4.15-4.45 (m , 2H), 4.55-4.9 (m, 3H9, 5.00 (d, 1 H, J = 8 Hz), 5.13 (m, 2H), 5.4-5.65 (m, 1 H), 6.16 (d, 1 H, J = 7 Hz), 7.05-7.4 (m, 10H). (3) .- In the same manner as described in Example 2- (7), 0.339 g (0.185 mmol) of the compound prepared in (2) was deprotected. above, with 0.36 g (5.54 mmol) of zinc, and then acylated with 0.100 g (0.221 mmol) of (R) -3-tetradecanoyloxytetradecanoic acid, in the presence of 0.068 g (0.276 mmol) of EEDQ, to give 0.25 g ( 71%) of N- (t-butyloxycarbonyl-methyl) -N - [(R) -3-tetradecanoyloxytetradecanoyl] -2-aminoethyl-2-deoxy-4-0-phosphono-2 - [(R) -3-tetradecanoyloxytetradecanoylamino] ] -3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -β-D-glucopyirase, as a colorless solid. (4) .- In the same manner as described in Example 2- (8), 0.25 was hydrogenated. g (0.131 mmol) of the compound prepared in (3) above, in the presence of 125 mg of platinum oxide, in 15 ml of 9 : 1 THF-AcOH. The crude hydrogenolysis product was dissolved in 1 ml of methylene chloride, cooled to 0 ° C and treated dropwise with 0.5 ml of TFA. After stirring for 2 hours at 0 ° C, the reaction mixture was concentrated and the residual RFA was removed by forming azeotropes with toluene. 0.23 g of the resulting residue was dissolved in 12 ml of 1% aqueous triethylamine, and lyophilized. Flash chromatography on silica gel with chloroform-methanol-water-triethylamine (gradient elution: 91: 8: 0.5: 05-85: 15: 05: 05) and subsequent purification, by acid extraction, as described in Example 2- (8), and lyophilization in 6 ml of 1% aqueous triethylamine, produced 99 mg (43%) of the triethylammonium salt of N- (carboxymethyl) -N - [(R) -3- tetradecanoyloxytetradecanoyl] -2-aminoethyl-2-deoxy-4-0-phosphono-2 - [(R) -3-tetradecanoyloxytetradecanoylamino] -3-0 - [(R) -3-tetradecanoyloxytetradecanoyl] -β-D-glucopyranoside, as a colorless solid, m.p. 162-163 ° C (decomposition): IR (film) 3286, 2922, 2852, 1732, 1651, 1556, 1455, 1434, 1378, 1260, 1088, 801 cm "1. NMR with (CDCl 3) delta 0.88 (t, 18H, J = around 6.5 Hz), 1.0-1.75 (m, 135H), 2.2-3.0 (m, 14H), 3.04 (c, 6H, J = 7.2 Hz), 3.25-3.8 (m, 5H), 3.85 -4.3 (m, 5H), 4.55 (d, 1 H, J = 7.5 Hz), 4.68 (d, 1 H, J = 8.1 Hz), 5.05-5.35 (m, 4H) Analysis calculated for C? 0oH? g2N2O? 9P.3H2 ?: C, 65.79; H, 10.60; N, 2.30; P, 1.70; Found: C, 65.82; H, 10.44; N, 2.40; P, 1.79.

EXAMPLE 29 (B28) PREPARATION OF N-CARBOXIMETHYL-N-r (R, -3-PECANOYLOXITETRADECANOIL-1-3-AMINOPROPYL-2-PESOXY-4-O-PHOSPHONO-2-r (R) - TRIETHYLMONIUM SALT) 3-PECANOYLOXITETRAPECANOILAMINOl -3-Or (R) -3-PECANOYLOXITETRAPECANOIL1-ß-P-GLUCOPIRANOSIPA. (COMPOUND (I) .R = R? = Ra = n-CgHigCO: X = Y = O: n = 1: m = p = 0: Ri = Rs = RB = Rg = H: R7 g CO? H: q = 1; Ra POaH?). (1) .- In the same manner as described in Example 2- (5), 450 mg (2.0 mmol) of the N- (3-hydroxypropyl) glycine benzyl ester was acylated with 1. 0 g (2.5 mmol) of (R) -3-decanoyloxytetradecanoic acid, in the presence of 900 mg (3.0 mmol) of EDC-Mel in methylene chloride, to give 0.76 g (63%) of the N- (3-hydroxypropyl) -N - [(R) -3-decanoyloxytetradecanoylglycine benzyl ester, as a colorless oil . 1 H NMR (CDCl 3) (1: 1 mixture of rotomeres) delta 0.88 (t, 6H, J = 6.6 Hz), 1.1-1.7 (m, 35H), 1.78 (m, 1 H), 2.26 (c, 2H, J = 7.6 Hz), 2. 37 and 2.54 (2 dd, 1 H, J = 14.9, 6.9 Hz), 2.60 and 2.89 (2 dd, 1 H, J = 14.8, 6.0 Hz), 3.51 (m, 4H), 3.70 (m, 1 H), 3.95-4.25 (m, 2H), 5.1-5.25 (m, 3H), 7.35 (m, 5H). (2) .- In the same manner as described in example 13- (5), 500 mg (0.83 mmol) of the compound prepared in (1) above and 1.0 g (0.83 mmol) of the compound prepared in the example were coupled. 15- (4), in the presence of 1. 07 g (4.15 mmol) of AgOTf, to give 1.27 g (72%) of the N- (benzyloxycarbonylmethyl) -N - [(R) -3-decanoyloxytetradecanoyl] -3-aminopropyl-2-deoxy-4-0 benzyl ester -diphenylphosphono-3-0 - [(R) -3-decanoyloxy-tetradecanoyl] -6-0- (2,2,2-trichloro-1,1-dimethylethoxycarbonyl) -2- (2,2,2-trichloroethoxycarbonylamino) -β-D-glucopyranoside. 1 H NMR (CDCl 3) (2: 1 mixture of rotomeres) delta 0.88 (t, 12H, J = 6.9 Hz), 1.1-1.7 (m, 60H), 1.80 (s, 3H), 1.88 (s, 3H), 2.1-2.6 (m, 11 H), 2.81 (dd, 1 H, J = 14.8, 6.2 Hz), 3.37 (m, 1 H), 3.52 (m, 2H), 3.76 (m, 1 H), 3.87 (m, 1 H), 4.05 (m, 2H); 4.28 (m, 3H), 4.62 (m, 3H), 4.77 (m, 1 H); 4.93 (d, 1 H, J = 8.2 Hz), 5.15 (m, 4H), 5.46 and 5.61 (2t, 1 H, J = 9.6 Hz), 5.95 and 6.045 (2d, 1 H, J = 7.4 Hz), 7.1-7.4 (m, 15H). (3) .- In the same manner as described in Example 2- (7), 1.25 g (0.71 mmol) of the compound prepared in (2) above, with 2.31 g (3.53 mmol) of zinc, was deprotected, and acylated with 353 mg (0.89 mmol) of (R) -3-decanoyloxytetrade-canoic acid, in the presence of 264 mg (1.07 mmol) of EEDQ to yield 670 mg (54%) of N-benzyloxycarbonylmethyl-N - [(R) -3-decanoyloxytetradecanoyl] -3-aminopropyl-2-deoxy-4-0-diphenylphosphono-3-0 - [(R) -3-decanoyloxytetradecanoyl] -2 - [(R) -3-decanoyloxytetradecanoylamino]) - ß-D -glucopyranoside, as an amorphous solid. (4) .- In the same manner as described in Example 2- (8), 670 mg (0.38 mmol) of the compound prepared in (3) above was hydrogenated, in the presence of 270 mg of palladium hydroxide on carbon and 200 mg. mg of platinum oxide, in 10: 1 EtOH / AcOH, to give 240 mg (39%) of the triethylammonium salt of N-carboxymethyl-N - [(R) -3-decanoyloxytetradecanoyl] -3-aminopropyl-2 -deoxy-4-0-phosphono-2 - [(R) -3-decanoyloxytetradeca-noylamino]) - 3-0 - [(R) -3-decanoyloxytetradecanoyl] -β-D-glucopyrene, as a white powder , pf 156-157 ° C. IR (film? 3284, 2929, 2853, 2729, 1732, 1655, 1628, 1551, 1466, 1378, 1314, 1164, 1108, 1047, 955, 844, 722 cm. "1. NMR with (CDCI3-CD3OD) delta 0.88 (t, 18 H, J = 6.9 Hz), 1.1-1.7 (m, 111 H), 2.27 (c, 6H, J = 6.2 Hz), 2.35-2.80 (m, 9H), 3.05 (c, 6H, J = 7.2 Hz), 3.25-3.60 (m, 4H), 3.75-4.10 (m, 4H), 4.23 (m, 2H), 4.47 (d, 1 H, J = 8.2 Hz), 4.61 (d, 1 H, J = 8.3 Hz), 5.05-5.25 (m, 4H). NMR with 13C (CDCI3) delta 173.4, 173.0, 171.1, 170.6, 170.3, 169.6, 100.5, 74.5, 73.9, 71.4, 71.2, 70.7, 70.2, 67.0, 65.8, 60.7, 54.6, 54.3, 51.4, 49.2, 46.0, 45.4, 42.1, 41.2, 39.4, 38.0, 37.7, 34.5, 34.3, 34.2, 34.2, 31.9, 29.8, 29.7, 29.6, 29.6, 29.2, 29.2, 29.2, 29.2, 29.2, 29.2, 28.2, 25.4, 25.3, 25.1, 22.7, 14.1, 11.1, 8.6 Analysis calculated for C89H? ON3O? 9P.H20: C, 65.37; H, 10.60; N, 2.57; P, 1.89; Found: C, 65.35; H, 10.42; N, 2.43; P. 2.05.

EXAMPLE PE TEST 1 STIMULATION PE PROPUCTION PEL ANTI-TETANUS TOXOIPE ANTIBODY The AGPs of the present invention increased the production of antibody to the purified tetanus toxoid, in a murine model. 10 mg of each AGP sample was added to 1 ml of an oil-lecithin mixture containing squalene oil plus 12% lecithin. The mixtures were heated in a water bath at 56 ° C, and sonically treated to obtain clear solutions. 50 μl of each solution was emulsified, stirring rapidly in 2 ml of saline with 0.1% Tween 80, preheated, containing 1.0 μg of the toxoid antigen / ml. The preparations were quickly stirred again just before they were administered to mice. Female C57BL / 6 x DBA / 2 F-i mice (8 per group) were treated with 0.2 ml of the appropriate preparation, distributed as a subcutaneous injection of 0.1 ml, on each side. The final dose for mouse, tetanus toxoid and AGP compounds was 0.2 μg and 50 μg, respectively. Control mice received tetanus toxoid in vehicle (oil-saline with Tween). All mice were treated on day 0, followed by a second immunization on day 21. Fourteen days after the second immunization the mice were bled and the sera were isolated by centrifugation.

Serum samples from each mouse were evaluated for anti-tetanus toxoid antibodies, by enzyme immunoassay (EIA) analysis, using microtiter plates coated with tetanus toxoid. The titers of anti-tetanus antibody for IgM, total Ig, as well as for the isotypes IgG-i, IgG2a and IgG2b- were evaluated. Each serum sample was diluted twice for eleven dilutions, starting with an initial dilution of serum of 1: 200. The results are shown in tables 2-4. or not. TABLE 2 ANTI-TETAL ANTIBODY ANTIBODY TITLES IN TREATED MICE "Reason T / C = experimental test title / Vehicle control title. r or cn n CUAPRO 3 TITLES PE ANTIBODY OF ANTI-TETANUS TOXOID IN TREATED MICE 'Reason T / C = experimental test titles / vehicle control titles.

NJ O n cn CUAPRO 4 TITLES OE ANTIBODY OEL TOXOIOE ANTI-TETANUS IN MICE TRATAPOS co "Reason T / C = experimental test title / vehicle control title.

The compounds of the present invention showed a dose response when administered with tetanus toxoid. Female BFDI mice (C57B1 / 6 X DBA / 2) (8 per group) were immunized with 0.2 ml of emulsions containing AGP + 0.2 μg of tetanus toxoid. A second immunization was administered 21 days after the primary immunization. Each mouse was bled 21 days after the second immunization. The results are shown in tables 5 and 6.

N > O n cn TABLE 5 RESPONSE TO AGP DOSES IN IMMUNIZED MICE WITH TOXOID OF TETANUS AC "Reason T / C = experimental test title + Vehicle control title NJ O cn cn TABLE 6 RESPONSE TO AGP DOSES IN IMMUNIZED MICE WITH TOXOID OF TETANUS C? 4-- M O n cn * T / C = experimental test title / vehicle control title co nd = not given. in EXAMPLE OF TEST 2 STIMULATION OF ANTI-OVOALBUMIN ANTIBODY PRODUCTION Female BDF1 mice (8 per group) were immunized with 0.2 ml of emulsions containing 50 μg of the AGP + 50 μg of ovalbumin. A second immunization was administered 21 days after the primary. Each mouse was bled 14 days after the second injection. The antibody titers of the immunized mice showing total IgG and IgM, as well as the titers for the IgG subgroups, including IgGi, IgG2a and IgG2b, are given in Table 7.

TABLE 7 ADJUVANT ACTIVITY IN IMMUNIZED BDF1 MICE WITH OVOALBUMIN * Reason T / C = Experimental test title / vehicle control title.

TABLE 7 (continued) * Reason T / C = Experimental test title / vehicle control title. The AGP compounds of the present invention, when administered to a warm-blooded animal with the ovalbumin antigen, stimulate the production of antibody to the antigen.

EXAMPLE OF TEST 3 GENERATION OF A PROTECTIVE IMMUNOLOGICAL RESPONSE TO INFECTIOUS INFLUENZA Mice vaccinated with formalin inactivated influenza and with the AGP compounds of the present invention, showed a protective immune response to a challenge with influenza, and also produced antibody for that antigen. The animals were vaccinated with the antigen and with the AGP compounds in various carriers. The degree of protection was determined by challenging the mice with intranasal (IN) administration of approximately 10 LD50 of infectious influenza A / HK / 68. The mortality was determined for 21 days after the challenge. The number of mice that survive the dose is a direct determination of the effectiveness of the vaccine. For the experiments provided, these data are not necessarily correlated with the amount of antibody produced. 1) .- Vaccines were formulated in a 0.2% solution of triethanoiamine (TeoA) / water containing: 1 hematoagglutinating unit (HAU) of inactivated influenza with formalin A / HK / 68 (Fl-Flu) and 50 μg of AGP, except vehicle control vaccines, which did not contain AGP. Only ICR mice (10 / group) were vaccinated once. The vaccines were administered by subcutaneous injection (SQ) of 0.1 ml / site in two different sites, near the inguinal lymph nodes, for a total of 0.2 ml of vaccine / mouse. Mice were bled (only five mice / group) from the orbital plexus, 14 days after vaccination. The sera were harvested and frozen at -20 ° C until they were used for enzyme-linked immunosorbent assay (ELISA). All mice were challenged 30 days after vaccination by intranasal (IN) administration of approximately 10 LD50 of infectious influenza A / HK / 68. The mortality was determined during the 21 days after the challenge. The anti-influenza antibody titers obtained from the vaccines with the TeoA formulations and the corresponding survival regimes of mice vaccinated with this formulation are shown in Table 8.

TABLE 8 ANTI-INFLUENZA ANTIBODY TITLES AND TREATED MICE SURVIVAL REGIMES 2) .- Vaccines were formulated in 2% squalene solution containing: 1 haemagglutinating unit (HAU) of inactivated influenza A with formalin A HK / 68 (Fl-Flu), and 25 μg of AGP, except for saline solution and vehicle control vaccines, which did not contain AGP. The BALB / c mice (1 O / group) were only vaccinated once. The vaccines were administered by subcutaneous injection (SQ) of 0.1 ml / site, in two different sites, near the inguinal lymph nodes for a total of 0.2 ml of vaccine / mouse. Mice were bled (only 5 mice / group) from the orbital plexus 14 days after vaccination. Sera were harvested and frozen at -20 ° C until used for enzyme-linked immunosorbent assay (ELISA). All mice were challenged 35 days after vaccination by intranasal (IN) administration of approximately 10 DL5o of infectious influenza A HK 68. Mortality was determined for 21 days after the challenge. Anti-influenza antibody titers obtained from vaccines with squalene formulations as well as the corresponding survival regimes of vaccinated animals are shown in Table 9.

TABLE 9 ANTI-INFLUENZA ANTIBODY TITLES AND 3) REGIMES. The antibody titers and the survival rate of the vaccinated mice were compared after a primary and then a secondary vaccination. The vaccines were formulated in 0.2% TeoA / water solution containing: 1 hemoagglutinating influenza inactivated with formalin A / HK / 68, 25 μg of AGP, except the vehicle control vaccine, which did not contain AGP. Vaccines were administered to ICR mice (20 / grp) by subcutaneous injection of 0.1 ml / site, at two different sites, near the inguinal lymph nodes, for a total of 0.2 ml of vaccine / mouse. Each group was divided into two subgroups, 35 days after the primary vaccination. One of each subgroup was challenged at this time; the remaining subgroups received a second vaccination. Mice were bled (only 5 / subgroup) from the orbital plexus, 14 days after vaccination (primary or secondary). The sera were harvested and frozen at -20 ° C until they were used for ELISA. The mice were challenged 35 days after primary or secondary vaccination, by means of intranasal administration of approximately 10 LD50 or 40 LD50 of infectious influenza A / HK 68, respectively. The mortality was determined during 21 days after the challenge. Anti-influenza antibody titers and survival regimens of mice after primary vaccination and secondary vaccination are shown in Table 10. Antibody titers, as well as survival regimens of mice vaccinated a second time, They were higher.

TABLE 10 ANTIBODY TITLES AND SURVIVAL REGIMES OF TREATED MICE EXAMPLE OF TEST 4 THE EFFECT OF THE LENGTH OF THE FATTY ACID CHAIN ON THE CAPACITY OF ADJUVANCE The effect of the length of the fatty acid chains R1-R3 on the activity was tested. Vaccines were formulated in 0.2% TeoA / water solution, containing 1 haemagglutinating unit of formalin inactivated influenza A / HK / 68 and 25 μg of AGP, except vehicle control vaccines, which did not contain AGP. ICR mice were vaccinated (1 O / group) only once. The vaccines were administered by subcutaneous injection of 0.1 ml / site in two different sites, near the inguinal lymph nodes, for a total of 0.2 ml of vaccine / mouse. Mice were bled (only five mice / group) from the orbital plexus 15 days after vaccination. Sera were harvested and frozen at -20 ° C until used for ELISA. All mice were challenged 35 days after vaccination, administering approximately 10 LD50 of infectious influenza A / HK / 68 intranasally. The mortality was determined during 21 days after the challenge. The length of the fatty acid chain seems to moderately affect biological activity. The results are shown in tables 11 and 12.

TABLE 11 ANTIBODY TITLES AND SURVIVAL REGIMES OF TREATED MICE TABLE 12 ANTIBODY TITLES AND SURVIVAL REGIMES OF TREATED MICE EXAMPLE OF TEST 5 THE EFFECT OF VARIATION IN THE CHAIN LENGTH BETWEEN THE X HETEROAT AND THE ATOM OF AGLLICON NITROGEN. ABOUT THE CAPACITY OF ADJUVANCY The length of the carbon chain between X and the aglycone nitrogen atom was progressively prolonged in a single atom. The effect of lengthening the chain between these two components on the adjuvant capacity was explored. Vaccines were formulated in 0.2% solution of TEoA / water containing 1 haemagglutinating unit of inactivated influenza with formalin A / HK / 68 and 25 μg of AGP, except vehicle control vaccines, which did not contain AGP. ICR mice (1 O / group) were vaccinated only once. The vaccines were administered by subcutaneous injection of 0.1 ml / site in two different sites, near the inguinal lymph nodes, for a total of 0.2 ml of vaccine / mouse. Mice were bled (only 5 mice / group) from the orbital plexus 14 days after vaccination. Sera were harvested and frozen at -20 ° C until used for ELISA. All mice were challenged 35 days after vaccination, by intranasal administration of approximately 10 LD50 of infectious influenza A / HK / 68. The mortality was determined during the 21 days following the challenge. It appears that the adjuvant activity is loosened as the length of the carbon chain increases between the hetero atom X and the aglycone nitrogen atom. However, depending on the residues attached to this carbon chain, the biological and metabolic stability of the molecules can be affected. The results are shown in table 13.

TABLE 13 ANTIBODY TITLES AND SURVIVAL REGIMES OF TREATED MICE EXAMPLE OF TEST 6 INDUCTION OF CYTOKINE BY AGP COMPOUNDS The AGP compounds of the present invention induced cytokines in ex vivo culture analysis of human whole blood. AGP compounds were solubilized in 10% EtOH-water and diluted to various concentrations. 50 μl of each dilution was added to 450 μl of human whole blood. The controls were treated with culture media (RPMI). The reaction mixture was incubated at 37 ° C for four hours with constant mixing on a rotator. 1.5 ml of sterile PBS was added to the reaction mixture; the cells were centrifuged and the supernatants removed for the cytokine test. The concentration of TNF-alpha and IL-1β was determined in each supernatant, using ELISA immunoassay equipment from R &D Systems. The results of these studies are shown in tables 14-19.

TABLE 14 STIMULATION OF THE CROCINA SECRETION IN AN EX VIVO ANALYSIS TABLE 15 STIMULUS OF CYTOKINES IN AN EX VIVO ANALYSIS "DAPC = too high to tell TABLE 16 STIMULUS OF CYTOKINES IN AN EX VIVO ANALYSIS TABLE 17 STIMULATION OF THE CROCINA SECRETION IN AN EX VIVO ANALYSIS TABLE 18 STIMULUS OF THE SECRETION OF CYTOKINE IN AN EX VIVO ANALYSIS TABLE 19 STIMULUS OF THE SECRETION OF CYTOKINE IN AN EX-LIVE ANALYSIS EXAMPLE OF TEST 7 STIMULUS OF A CYTOTOXIC RESPONSE IN LYMPHOCYTE T The induction of a cytotoxic response in T lymphocyte was detected after administering the AGP compounds of the present invention and a protein antigen, by means of a cytotoxicity analysis. Groups of C57BL / 6 mice were administered a primary immunization subcutaneously (in the inguinal region) of 25 μg of ovalbumin (OVA) formulated in AGP preparations. The volume injected was 200 μl. Twenty-one days later, three mice were killed for each experimental group and the spleens were removed and collected as single-cell suspensions and counted. 75 x 106 spleen cells were placed in 3-4 ml of medium, from the experimental groups, in a 25 cm2 T-flask. Then 1.0 ml of irradiated E.G7 (OVA) cells at 20,000 rads, at 5 x 106 / ml, was added to the flask. The volume was brought to 10 ml. The cultures were maintained by vertically placing the T flasks in an incubator at 37 ° C, 5% C02, for four days. On day 4, the surviving cells of the flasks were recovered, washed once in fresh medium and resuspended in 5.0 ml and counted. The recovered effector cells were adjusted to 5 x 10 6 viable cells / ml and volumes of 100 μl were diluted in triplicate in concavities of 96 concavity round bottom plates (Corning 25850), using 100 μl / concavity of medium, as diluent. Volumes of 100 μl of 51 Cr-labeled targets were added to the concavities (see below) [EL-4 cell line of ovalbumin gene from E.G7 (OVA)] at 1 x 105 cells / ml, to the concavities. Concavities of spontaneous release (SR) contained 100 μl of blanks and 100 μl of medium. The concavities of Maximum release (MR) contained 100 μ of white and 100 μ of detergent (2% of Tween 20). The effector / target (E / T) ratios were 50: 1, 25: 1, 12. 5: 1 The plates were centrifuged at 400 x g and incubated at 37 ° C, 5% C02, for four hours. After incubation the supernatants were collected from concavity using a Skatron supernatant collection system. % specific lysis 100 X (Exp. Release - SR) (MR - SR) The target cells, E.G7 (OVA) were labeled with 51Cr (sodium chromate) as follows. It was mixed in a total volume of 1. 0 ml, 5 x 106 white cells and 250 μCi of 51 Cr in 15 ml of conical tube.

The cell suspensions were incubated in a water bath at 37 ° C for 90 minutes, mixing gently every 15 minutes. After incubation washed the labeled cells three times, by centrifugation, and decanted with volumes of 15 ml of medium. After the third centrifugation, re-suspended the cells in 10 ml of fresh medium and allowed to stand room temperature for 30 minutes, and then centrifuged. Finally the cells were resuspended in medium at 1 x 10 5 cells / ml.

Mice immunized according to the above procedure, with the AGPs of the present invention exhibited a cytotoxic T lymphocyte response to the OVA antigen, as shown in Table 20.

TABLE 20 CITOTOXIC RESPONSE OF LYMPHOCYTE T IN TREATED CELLS EXAMPLE OF TEST 8 GENERATION OF SERUM AND MUCOSAL ANTIBODY TITLES FOR TOXOID OF TETANUS The AGPs of the present invention elicited an immunological response of both serum and mucosal to the purified tetanus toxoid when administered intranasally. Groups of BALB / c mice were given a primary immunization (1 °) with 10 μg of tetanus toxoid (TT) + 20 μg of AGP, formulated in an aqueous formulation (FA), with a volume of 20 μl. A secondary immunization was given (2 °) 14 days later, and a tertiary immunization (3o) of identical composition to the first and second, was administered 14 days later. The mice were bled on day 21 (day 7 after 2o) and day 38 (day 10 after 3 °) and day 48 (day 20 after 3o). Vaginal wash / faecal extract samples were taken on day 7 after 2o and day 7 after 3o. The serum and wash samples for the anti-TT antibody were analyzed by common and current ELISA methods. The results of these analyzes are shown in tables 21 and 22 below. The aqueous formulation comprises the AGPs of the present invention and one or more surfactants. Surfactants useful in an aqueous composition include glycodeoxycholate, deoxycholate, sphingomyelin, sphingosine, phosphatidylcholine, 1,2-dimyristoyl-sn-glycero-3-phosphoethanol-amine, L-alpha-phosphatidylethanolamine and 1,2-dipalmitoyl-sn-glycero. -3-phosphocholine, or a mixture of them. The aqueous formulation used in this example comprises the surfactant 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and was prepared as follows: Briefly, a 4 mg / ml solution of DPPC was prepared in ethanol. An aliquot of the ethanolic solution was added to the dry AGP and gently shaken to wet the AGP. The ethanol was removed by blowing a stream of filtered nitrogen, gently, over the flask. Water was added for injection and the suspension was sonically treated for 10 minutes at 60 ° C, until it was clear. The resulting aqueous formulation contains approximately 118 μg / ml of DPPC, has particles of around 70 nm and is filter sterilized.

TABLE 21 ANTI-TETANUS TOXOID ANTIBODY TITLES IN TREATED MICE Title of anti-tetanus toxoid-1 N > O cn cn TABLE 22 ANTI-THERAPY SERUM ANTIBODY TITLES FOR ANTI-TETANUS IN TREATED ANIMALS SERUM meetings, Title 1 of anti-tetanus toxoid CD O intranasal administration of TT formulated in AGP-AF induj immunological humoral, specific for the antigen or an immunological mucous response (Table 21) a is EXAMPLE OF TEST 9 FROM AN IMMUNE RESPONSE TO ANTIGEN IAL HEPATITIS B, THROUGH ADMINISTRATION INTRANASAL Hepatitis B surface antigen (HbsAg), administered to mice, together with the compounds of the present invention and IgG and IgA in serum for that antigen. Ig was detected two vaginal and the induction of a response was detected ocito T by cytotoxicity analysis. Groups of BALB / c mice were given a primary immunization 16 days after secondary immunization (d16 post 2 °) and 8 days after tertiary immunization (dd post 3 °). The antibody titers of serum and mucosal were determined at 22 days after secondary immunization (d22 post 2o) and 21 days after tertiary immunization (d21 post 3o). Antibody analyzes were carried out by ordinary and common ELISA methods. Of carried out cytotoxicity analysis as described in test example 7. The results of this experiment are shown in tables 23-26.

TABLE 23 CITOTOXIC RESPONSE TO LYMPHOCYTE T OF TREATED CELLS TABLE 24 CYTOTOXIC RESPONSE OF T LYMPHOCYTE IN TREATED CELLS TABLE 25 ANTIHEALTH ANTIBODY TITLES IN TREATED MICE * day22post2 °; #K = 103 TABLE 26 ANTI-HEPATITIS ANTIBODY TITLES IN TREATED MICE "day 21 post 3 °; #K = 103 Groups of BALB / c mice were immunized with 2.5 μg of HbsAg + 10 μg of AGP-AF, intranasally, and strengthened intranasally with 7.5 μg of HbsAg + 10 μg AGP-AF, 21 days later. Vaginal samples were collected 10 days after the booster immunization and analyzed for the anti-HbsAg antibody. The results of this analysis are shown in table 27.

TABLE 27 The intranasal administration of HbsAg with the compounds of the present invention stimulated both the humoral and the cellular immune response to that antigen. Intranasal immunization with the antigen formulated in AGP-AF induced a cytotoxic T lymphocyte response (Tables 23-24) and humoral immunological responses specific for the antigen (Tables 25 and 26) and mucosal (Table 27).

EXAMPLE OF TEST 10 GENERATION OF A PROTECTIVE IMMUNOLOGICAL RESPONSE AGAINST INFLUENZA Mice immunized intranasally with FLUSHIELD influenza vaccine containing hemagglutinin antigen and the AGPs of the present invention, produced both IgG and IgA, which were recovered in vaginal washings. The immunized mice were also protected against the subsequent challenge with influenza. ICR mice were immunized three times at 21-day intervals, intranasally, with FLUSHIELD influenza vaccine (Wyeth-Lederle) containing 0.3 μg of haemagglutinin antigen (HA) + 10 μg of AGP-AF or thermally labile enterotoxin (LT) of Recombinant E. coli. AGP-AF was prepared as in test example 8. LT was solubilized in saline at 1 μg / ml. Vaginal washes were collected 14 days after the second and third immunizations. Serum samples were collected 14 days after the third immunization. The mice were challenged with 10 LD50 (lethal dose 50) of infectious influenza A / HK 68 thirty-five days after the final immunization, and monitored for mortality. Tables 28 and 29 show the results of analyzes performed by common and current ELISA methods to detect anti-influenza antibody titers in vaginal and serum washes.

TABLE 28 TABLE 29 These data demonstrate that AGP in AF, when administered intranasally, act as mucosal adjuvants, causing the production of IgA in mucosal sites. Increased protection was also induced against a pathogen of the upper respiratory tract, which invades through the mucosa.

EXAMPLE OF TEST 11 GENERATION OF IMMUNOLOGICAL RESPONSES FROM STABLE EMULSION FORMULATIONS The AGP compounds of the present invention stimulated both humoral and cytotoxic T lymphocyte responses when formulated in a stable emulsion (ES). AGPs were tested at 25 μg dose levels to adjuvant hepatitis B surface antigen (HbsAg) for the induction of CTL and antibody responses. BALB / c mice were immunized subcutaneously with 2.0 μg of HbsAg plus 25 μg of AGP / SE on day 0 and day 21. The CTL analysis was carried out as in test example 7. The AGP was formulated in an emulsion stable (SE) and the AGP-SE compositions were designated. The methods for preparing the stable emulsion containing 10% volume / volume of squalene, 0.091% weight / volume of PLURONIC-F68 block copolymer, 1.909% weight / volume of phosphatidylcholine, 1.8% volume / volume of glycerol, 0.05% by weight / volume of alpha-tocopherol, 10% of ammonium phosphate buffer and 78.2% by volume / volume of water for injection, should be readily apparent to those who are experts in the field. The emulsion was homogenized to a particle size of < 0.2 μm. Table 30 shows that the AGPs of the present invention induced a cytotoxic response of T lymphocyte to HbsAg.

TABLE 30 RE CYTOTOXIC SETTING OF LYMPHOCYTE T IN TREATED CELLS The results of the antibody titer for HbsAg are shown in Table 31. The sera of the indentations taken on day 28 after 2 ° were titrated on ELISA plates coated with HbsAg or with a peptide of 28 amino acids (p72) containing epitopes. of B cells found in the S antigen region, residues 110-137 of HbsAg.

TABLE 31 TITLE ANTI-HbsAq OF TREATED MICE Mice treated with AGP-SE exhibited humoral (Table 31) and cytotoxic T lymphocyte responses in the hepatitis B surface antigen. Interestingly, mice treated with AGP-SE in serum exhibited a specific antibody titer for vigorous IgG2a, detected for both antigens; whereas vehicle-SE only induced a modest response to IgG2a. It should be understood that the foregoing examples are merely illustrative of the present invention. Certain modifications of the compositions and / or methods employed can be made, and still achieve the objects of the invention. Said modifications are contemplated as if they were within the scope of the invention REFERENCES Bulusu, M.A.R-C. Waldstattend P., Hildebrandt, J., Schütze, E. and G. Schulz (1992) Cyclic Analogues of Lipid A: Synthesis and Biological Activities, J Med Chem. 35: 3463-3469. Ikeda K., Asahara, T. and K. Achiwa (1993) Synthesis of Biologically Active N-acylated L-serine-Containing Glucosamine-4-Phosphate Derivatives of Lipid A, Chem Pharm Bull. 41 (10): 1879-1881. Miyajima, K-, Ikeda, K. and K. Achiwa (1996) Lipid A and Related Compounds XXXI, Synthesis of Biologically Active N-Acylated L-Serine-Containing D-Glucosamine 4-Phosphate Derivatives of Lipid A, Chem. Pharm. Bull. 44 (12): 2268-2273. Shimizu, T., Akiyama, S., Masuzagawa T., Yanagihara Y., Nakamoto, S., Takahashi T., Ikeda, K. and K. Achiwa (1985) Antitumor Activity and Biological Effects of Chemically Synthesized Monosaccharide Analogues of Lipid A in Mice. Chem. Pharm. Bull. 33 (10): 4621-4624. Shimizu T., Sugiyama, K., Iwamoto, Y., Yanagihara Y., Asahara, T., Ikeda, K. and K. Achíwa (1995) Biological Activities of Chemically Synthesized N-acylated Serine-linked Lipid A Analog in Mice , Int. J Immunopharmac, 16 (8): 659-665. Shimizu, T., lida, K., Iwamoto, Y., Yanagihara, Y., Ryoyama, K..Asahara T., Ikeda, K. and K. Achiwa (1995) Biological Activities and Antitumor Effects of Synthetic Lipid A Analogs L? N? Ed N-Acylated Serine, Int. J.

Immunopharmac, 17 (5): 425-431.

Claims (1)

NOVELTY OF THE INVENTION CLAIMS 1. - An immuno-effector compound, characterized in that it has the following structure: (I) where X is selected from the group consisting of O and S; And it is selected from the group consisting of O and NH; n, m, p and q are integers from 0 to 6; Ri, R2 and R3 are the same or different and are normal fatty acyl residues having approximately 7 to 16 carbon atoms; R4 and R5 are identical or different and are selected from the group consisting of H and methyl; R6 and R7 are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxi, amino, mercapto, cyano, nitro, formyl and carboxy; and its esters and amides; and R8 and R9 are the same or different and are selected from the group consisting of phosphono and H; and at least one of R8 and R9 is phosphono. 2. - The compound according to claim 1, further characterized in that R8 is carboxy. 3. - The compound according to claim 2, further characterized in that X is O; Cast; n, m, p and q are 0; R-i, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, R5 and R7 are H; R8 is phosphono; R9 is H; each of R-i, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a configuration S. 4. - The compound according to claim 2, further characterized in that X is O; Cast; n, m, p and q are 0; R-i, R2 and R3 are normal fatty acyl residues having 12 carbon atoms; R4, R5 and R7 are H; R8 is phosphono; R9 is H; each of R1, R and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. 5. - The compound according to claim 2, further characterized in that X is O; And it is O, n, m, p and q are 0; Ri, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4, R5 and R7 are H; R8 is phosphono; R9 is H; each not of R1, R and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having an R configuration. 6. - The compound according to claim 2, further characterized in that X is O; Cast; n, m, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 8 carbon atoms; R4, R5 and R are H; R8 is phosphono; R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and R5 is attached to a stereogenic center having a S configuration. 7. - The compound according to claim 1, further characterized in that Rβ is H. 8. - The compound according to claim 7, further characterized in that X is O; Cast; n is 2; m, p and q are 0; R1 t R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, R5 and R7 are H; R8 is phosphono; R9 is H; each of R-i, R2 and R3 is attached to a stereogenic center having an R configuration. 9. - The compound according to claim 7, further characterized in that X is O; Cast; n is 1; m and p are 0; q is 1; R1 t R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R and R5 are H; R7 is carboxy; R8 is phosphono; R9 is H; each of R ^ R2 and R3 is attached to a stereogenic center having a configuration R. 10. The compound according to claim 7, further characterized in that X is O; Cast; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, R5 and R7 are H; R8 is phosphono; R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having a configuration R. 11. The compound according to claim 7, further characterized in that X is O; Cast; m, n, p and q are 0; R1 t R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4, R5 and R7 are H; R8 is phosphono; R9 is H; each of R-i, R2 and R3 is attached to a stereogenic center having a configuration R. 12. The compound according to claim 7, further characterized in that X is O; Cast; m, p and q are 0; n is 1; R1 t R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R, R5 and R7 are H; R8 is phosphono; R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. 13. The compound according to claim 1, further characterized in that R & It is hydroxy. 14. The compound according to claim 13, further characterized in that X is O; Cast; m, n and q are 0; p is 1; R1 f R2 and R3 are normal fatty acyl residues having 12 carbon atoms; R4 and R5 are H; R7 is H; R8 is phosphono; and R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an S configuration. 15. The compound according to claim 13, further characterized in that X is O; Cast; m and q are 0; n and p are 1; Ri, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4, R5 and R7 are H; R7 is H; R8 is phosphono; and R9 is H; each of R1 (R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a S configuration. 16. The compound according to claim 13, further characterized by X is O, Y is O, m, n and q are 0, p is 2, R1 t R2 and R3 are normal fatty acyl residues having 10 carbon atoms, R4, R5 and R7 are H, R8 is phosphono, and R9 is H, each of Ri, R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having an S configuration. 17. The compound according to claim 13, further characterized because X is O, Y is O, m, n and q are 0, p is 1, R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms, R4, R5 and R7 are H, R8 is phosphono; R9 is H, each of R1 f R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereo center gene having an R configuration. 18. The compound according to claim 13, further characterized in that X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, R5 and R7 are H; R8 is phosphono; and R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a configuration S. 19. - The compound according to claim 13, further characterized in that X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 11 carbon atoms; R4, R5 and 7 are H; R8 is phosphono; and Rg is H; each of R1, R and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a configuration S. 20. - The compound according to claim 13, further characterized in that X is O; Cast; m, n and q are 0; p is 1; R ^ R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4, R5 and R7 are H; R8 is phosphono; and Rg is H; each of R-i, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a configuration S. 21. - The compound according to claim 13, further characterized in that X is O; Cast; m, n, p and q are 0; R1 f R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4 and R5 are H; Rβ is aminocarbonyl; R is H; R8 is phosphono; and R9 is H; each of R-i, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a configuration S. 22. - The use of a compound that has the following structure: (I) where X is selected from the group consisting of O and S; And it is selected from the group consisting of O and NH; n, m, p and q are integers from 0 to 6; Ri, R2 and R3 are normal fatty acyl residues having approximately 7 to 16 carbon atoms; R4 and R5 are the same or different and are selected from the group consisting of H and methyl; Rβ and R7 are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxi, amino, mercapto, cyano, nitro, formyl and carboxy; and its esters and amides; and Rβ and Rg are the same or different and are selected from the group consisting of phosphono and H; and at least one of Rβ and Rg is phosphono, for the manufacture of a medicament for increasing the immune response of a mammal. 23. The use according to claim 22, wherein R6 in said compound is carboxy. 24. The use according to claim 23, wherein said compound has the following structure: X is O; Cast; n, m, p and q are 0; Ri, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4 and R5 are H; R7 is H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. The use according to claim 23, wherein said compound has the following structure: X is O; Cast; n, m, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 12 carbon atoms; R4 and R5 are H; R7 is H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. The use according to claim 23, wherein said compound has the following structure: X is O; Cast; n, m, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, R5 and R are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having an R configuration. 27. - The use according to claim 23, wherein said compound has the following structure: X is O; Cast; n, m, p and q are 0; Ri, R2 and R3 are normal fatty acyl residues having 8 carbon atoms; R4, R5 and R7 is H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. 28. - The use according to claim 22, wherein Rβ in said compound is H. 29. - The use according to claim 28, wherein said compound has the following structure: X is O; Cast; n is 2, m, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, R5 and R7 are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. 30. - The use according to claim 28, wherein said compound has the following structure: X is O; Cast; n is 1, m and p are 0; q is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R, R5 and R7 are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. 31. - The use according to claim 28, wherein said compound has the following structure: X is O; Cast; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, Rs and 7 are H; Rß is phosphono; R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. The use according to claim 28, wherein said compound has the following structure: X is O; Cast; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, Rs and R7 are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. 33. The use according to claim 28, wherein said compound has the following structure: X is O; Cast; m, p and q are 0; n is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, R5 and R7 are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having a configuration R. 34.- The use according to claim 22, wherein Rβ in said compound is hydroxy. 35.- The use according to claim 34, wherein said compound has the following structure: X is O; Cast; m, n and q are 0; p is 1 R1, R2 and R3 are normal fatty acid residues having 12 carbon atoms; R4l and Rs are H; R7 is H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and R5 is attached to a stereogenic center having a S configuration. The use according to claim 34, wherein said compound has the following structure: X is O; Cast; m, and q are 0; n and p are 1; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4, Rs and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and Rs is attached to a stereogenic center having a S configuration. The use according to claim 34, wherein said compound has the following structure: X is O; Cast; m, n and q are 0; p is 2; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, Rs and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and R5 is attached to a stereogenic center having a S configuration. The use according to claim 34, wherein said compound has the following structure: X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, Rs and 7 are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and R5 is attached to a stereogenic center having a configuration R. 39.- The use according to claim 34, wherein said compound has the following structure: X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R, R5 and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and R5 is attached to a stereogenic center having a S configuration. The use according to claim 34, wherein said compound has the following structure: X is O; Cast; m, n and q are 0; p is 1 Ri, R2 and R3 are normal fatty acyl residues having 11 carbon atoms; R, Rs and Rr are H; Rß is phosphono; Rg is H; each of R1 (R2 and R3 is attached to a stereogenic center having an R configuration and Rs is attached to a stereogenic center having a S configuration. The use according to claim 34, wherein said compound has the following structure: X is O, Y is O, m, n and q are 0, p is 1, R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms, R4, Rs and Rr are H, R7 is H; Rβ is phosphono; Rg is H, each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and Rs is attached to a stereogenic center having a S configuration. with claim 22, wherein said compound has the following structure: X is O; Y is O; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; and Rs are H, Rr is H, R6 is aminocarbonyl, Rr is H, Rβ is phosphono, Rg is H, each of R1, R2 and R3 is attached to a stereo center. nico having an R configuration and R5 is attached to a stereogenic center having an S configuration 43. A vaccine composition, comprising a compound having the following structure: (i) where X is selected from the group consisting of O and S; And it is selected from the group consisting of O and NH; n, m, p and q are integers from 0 to 6; R1, R2 and R3 are the same or different and are normal fatty acyl residues having approximately 7 to 16 carbon atoms; R4 and Rs are the same or different and are selected from the group consisting of H and methyl; Rβ and Rr are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxi, amino, mercapto, cyano, nitro, formyl and carboxy; and its esters and amides; and Rβ and Rg are the same or different and are selected from the group consisting of phosphono and H; and at least one of Rβ and Rg is phosphono. 44. The composition according to claim 43, further characterized in that said composition comprises the said compound wherein Rβ is carboxy. 45.- The composition according to claim 44, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; n, m, p and q are 0; Ri, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, Rs and Rr are H; Rß is phosphono; Rg is H; each of R1 f R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. The composition according to claim 44, further characterized in that said composition it comprises the compound having the following structure: X is O; And it is O, n, m, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 12 carbon atoms; R4, Rs and R7 are H; Rß is phosphono; Rg is H; each not of R1, R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. The composition according to claim 44, further characterized in that said The composition comprises the compound having the following structure: X is O; Cast; n, m, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, Rs and Rr are H; R6 is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and Rs is attached to a stereogenic center having an R configuration. 48. The composition according to claim 44, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; n, m, p and q are 0; R1t R2 and R3 are normal fatty acyl residues having 8 carbon atoms; R4, Rs and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and Rs is attached to a stereogenic center having a S configuration. The composition according to claim 43, further characterized in that said composition it comprises the compound in 50. The composition according to claim 49, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; n is 2; m, p and q are 0; R1; R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R, R5 and Rr are H; Rß is phosphono; R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having a configuration R. 51. The composition according to claim 49, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; n is 1; m and p are 0; q is 1; Ri, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R and R5 are H; R7 is carboxy; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. 52. - The composition according to claim 49, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R, R5 and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. 53. - The composition according to claim 49, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; m, n, p and q are 0; R1 t R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4, R5 and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. 54. - The composition according to claim 49, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; m, p and q are 0; n is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, Rs and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. 55. - The composition according to claim 43, further characterized in that the composition comprises the compound wherein Rβ is hydroxy. 56. - The composition according to claim 55, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; R1 f R2 and R3 are normal fatty acyl residues having 12 carbon atoms; R4 and Rs are H; R7 is H; Rß is phosphono; and Rg is H; each of Ri, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a configuration S. 57. - The composition according to claim 55, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m and q are 0; n and p are 1; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4, Rs and Rr are H; R7 is H; Rß is phosphono; and Rg is H; each of R1 (R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. 58. - The composition according to claim 55, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 2; R1 (R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, Rs and Rr are H; Rß is phosphono; and R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a S configuration. The composition according to claim 55, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, Rs and Rr are H; Rß is phosphono; and Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an R configuration. The composition according to claim 55, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; R1, R and R3 are normal fatty acyl residues having 14 carbon atoms; R, R5 and Rr are H; Rß is phosphono; and R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an S configuration. The composition according to claim 55, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 11 carbon atoms; R, R5 and Rr are H; Rß is phosphono; and R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and Rs is attached to a stereogenic center that has a configuration S. 62. - The composition according to claim 55, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; Ri, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, Rs and Rr are H; Rß is phosphono; and Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having a configuration R; and R5 is attached to a stereogenic center having a S configuration. The composition according to claim 21, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4 and R5 are H; R6 is aminocarbonyl; Rr is H; Rß is phosphono; and Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an S configuration. - A pharmaceutical composition, characterized in that it comprises a compound having the following structure: (I) where X is selected from the group consisting of O and S; And it is selected from the group consisting of O and NH; n, m, p and q are integers from 0 to 6; Ri, R2 and R3 are normal fatty acyl residues having approximately 7 to 16 carbon atoms; R and R5 are the same or different and are selected from the group consisting of H and methyl; Rβ and Rr are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxi, amino, mercapto, cyano, nitro, formyl and carboxy; and its esters and amides; and Rβ and Rg are the same or different and are selected from the group consisting of phosphono and H; and at least one of Rβ and Rg is phosphono. The composition according to claim 64, further characterized in that said composition comprises the said compound wherein Rβ is carboxy. 66.- The composition according to claim 65, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; n, m, p and q are 0; R1 f R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, R5 and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. The composition according to claim 65, further characterized in that said The composition comprises the compound having the following structure: X is O; And it is O, n, m, p and q are 0; R ^ R2 and R3 are normal fatty acyl residues having 12 carbon atoms; R4, Rs and Rr are H; Rß is phosphono; Rg is H; each not of R1, R2 and R3 is fixed to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having a S configuration. The composition according to claim 65, further characterized in that said The composition comprises the compound having the following structure: X is O; Cast; n, m, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4, Rs and Rr are H; Rß is phosphono; Rg is H; each of Ri, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having a configuration R. 69.- The composition according to claim 65, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; n, m, p and q are 0; RL R2 and R3 are normal fatty acyl residues having 8 carbon atoms; R4, Rs and Rr are H; Rß is phosphono; R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration and R5 is attached to a stereogenic center having a S configuration. The composition according to claim 64, further characterized in that said composition comprises the compound wherein R6 is H. 71. The composition according to claim 70, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; n is 2; m, p and q are 0; R ^ R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, R5 and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having a configuration R. 72. The composition according to claim 70, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; n is 1; m and p are 0; q is 1; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R and Rs are H; Rr is carboxy; Rß is phosphono; Rg is H; each of Ri, R2 and R3 is attached to a stereogenic center having a configuration R. 73. The composition according to claim 70, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R4, Rs and Rr are H; Rß is phosphono; R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. The composition according to claim 70, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, R5 and Rr are H; Rß is phosphono; R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration. The composition according to claim 70, further characterized in that said composition comprises the compound having the following structure: X is O; Cast; m, p and q are 0; n is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R, Rs and Rr are H; Rß is phosphono; Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having a configuration R. 76. The composition according to claim 64, further characterized in that the composition comprises the compound wherein Rβ is hydroxy. 77. - The composition according to claim 76, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; Ri, R2 and R3 are normal fatty acyl residues having 12 carbon atoms; R4 and R5 are H; R7 is H; Rß is phosphono; and Rg is H; each of R1 (R2 and R3 is attached to a stereogenic center having an R configuration, and R5 is attached to a stereogenic center having an S configuration. The composition according to claim 76, further characterized in that the The composition comprises the compound having the following structure: X is O, Y is O, myq are 0, n and p are 1, R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms, R, R5 and R7 are H; R7 is H; Rβ is phosphono; and Rg is H, each of R1, R2 and R3 is attached to a stereogenic center having an R configuration, and Rs is attached to a stereogenic center having an S configuration. - The composition according to claim 76, further characterized in that the composition comprises the compound having the following structure: X is O, Y is O, m, n and q are 0, p is 2, R1, R2 and R3 are residues of normal fatty acyl that have 10 carbon atoms; R4, Rs and R7 so n H; Rβ is phosphono; and Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an S configuration. The composition according to claim 76, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; Ri, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R, Rs and Rr are H; Rß is phosphono; and R9 is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an R configuration. The composition according to claim 76, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 14 carbon atoms; R, Rs and Rr are H; Rß is phosphono; and Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an S configuration. The composition according to claim 76, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 11 carbon atoms; R4, R5 and Rr are H; R8 is phosphono; and Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an S configuration. The composition according to claim 76, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n and q are 0; p is 1; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R, Rs and Rr are H; Rß is phosphono; and Rg is H; each of R1, R2 and R3 is attached to a stereogenic center having an R configuration; and R5 is attached to a stereogenic center having an S configuration. The composition according to claim 43, further characterized in that the composition comprises the compound having the following structure: X is O; Cast; m, n, p and q are 0; R1, R2 and R3 are normal fatty acyl residues having 10 carbon atoms; R4 and Rs are H; R6 is aminocarbonyl; R7 is H; Rß is phosphono; and R9 is H; each of R1, R2 and 3 is attached to a stereogenic center having an R configuration; and Rs is attached to a stereogenic center having an S configuration. The composition according to claim 64, further characterized in that the pharmaceutically acceptable carrier is an aqueous composition comprising water and one or more surfactants selected from the group consisting of: consists of glycodeoxycholate, deoxycholate, sphingomyelin, sphingosine, phosphatidylcholine, 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine, L-alpha-phosphatidylethanolamine and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine, or a mixture of they. 86.- The composition according to claim 85, further characterized in that said one or more surfactants are 1,2-dipalmitoyl-sn-glycero-3-phosphocholine. 87. The composition according to claim 85, further characterized in that the molar ratio of said compound to the surfactant is from about 10: 1 to about 10: 5. 88. - The composition according to claim 85, further characterized in that the molar ratio of said compound to the surfactant is about 4: 1. 89. The composition according to claim 64, further characterized in that the carrier is a stable emulsion comprising a metabolizable oil; one or more surfactants; an antioxidant and a component to make the emulsion isotonic. 90.- The composition according to claim 89, further characterized in that the stable emulsion comprises 10% volume / volume of squalene; 0.9% by weight / volume of PLURONIC F68 block copolymer; 1.9% weight / volume of egg phosphatidylcholine;

1. 75% volume / volume of glycerol and 0.05% weight / volume of alpha-tocopherol.