JP2882840B2 - Novel antiviral agent and method for producing the same - Google Patents

Description

The present invention relates to a novel antiviral agent 2 ', 3', 4'-trideoxygluconucleoside represented by the general formula [I], and It relates to a manufacturing method.

[Conventional technology]

In recent years, with the rapid increase of diseases caused by viruses such as AIDS and hepatitis, various antiviral agents are being developed. Among these, for example, AZT (azidothymidine) against HIV (AIDS virus) and ACV (acyclovir) effective against HSV (herpes simplex virus) are known.

[Problems to be solved by the invention]

A common problem with previously developed antiviral agents lies in their limited antiviral spectrum. For example, ACV has no effect on HIV and AZT does on HSV.
Does not exhibit its effect. That is, certain antiviral agents are effective only for certain viruses.

Therefore, development of a new antiviral agent having a broader antiviral spectrum is awaited.

In addition, if the antiviral agent is used for a long time as a fate, a resistant strain of virus appears. For this reason,
Long-term use is impossible just because it is a highly effective drug. Therefore, development of a new antiviral agent having a different site of action is expected even as a concomitant drug with an existing antiviral agent.

An object of the present invention is to provide a novel antiviral agent having new efficacy and a method for synthesizing the same.

[Means for solving the problem]

General formula [I] (Wherein R ₁ is a hydrogen atom, a hydroxyl group, an amino group, an alkyl group,
Is a halogen atom, an alkoxy group, or a mercapto group, and R ₂ and R ₃ are a hydrogen atom or an amino group, respectively.) It is based on that.

The present invention provides a compound represented by the above general formula [I].
The present invention relates to a novel antiviral agent comprising at least one of 3 ', 4'-trideoxyglucopurine nucleosides as an active ingredient, and a method for producing the same.

In the present invention, the purine derivative represented by the general formula [IV] can be used as it is from inexpensive ribonucleic acid components, or the ribonucleic acid components are chemically modified by a well-known method. Can be used. Alternatively, a purine base derivative synthesized by total synthesis may be used. Further, those already on the market can also be used.

Further, in the present invention, 2,2 represented by the general formula [III]
3,4-trideoxyglucopyranose is inexpensive,
Further, it can be easily derived and synthesized from easily available ethyl 2-oxocyclopentanecarboxylate.

(Operation)

The antiviral activity of the 2 ', 3', 4'-trideoxygluconucleosides (hereinafter abbreviated as 3dGN) of the present invention will be described below.

The antiviral action of the 2 ', 3', 4'-trideoxygluconucleosides (3dGN) of the present invention mainly has two points.

First, as the first point, the sugar moiety of 3dGN has a glucose structure, and this structure resembles ribose, so that viral enzymes (kinase, deaminase, etc.) mistake 3DGN for DNA-constituting nucleic acids. As a result, 3dGN
Exerts antiviral effects by antagonizing viral enzymes and delaying the synthesis of viral DNA.

Next, the second point is that 3dGN has a structure having only one hydroxyl group at the 6'-position, so that once incorporated into viral DNA, the next nucleoside cannot bind. That is,
3dGN directly inhibits viral replication as a viral DNA chain terminator.

Existing antiviral agents such as AZT and ACV also exhibit an antiviral effect by a similar action.
GN has a different effect from existing antiviral agents for the following reasons.

That is, since 3dGN has 2 ′, 3 ′, 4′-trideoxyglucose having a flexible cyclic structure in the sugar moiety, it can express a broad antiviral spectrum.

For example, in the case of AZT, the sugar moiety is a relatively rigid five-membered ribose, so the distance between the base moiety and the hydroxyl group of the sugar is constant, and follows the viral enzyme that changes as the virus type changes Can not. This results in a relatively narrow antiviral spectrum. However, the present invention
3dGN has a glucose skeleton, which is a relatively flexible six-membered ring, in its sugar moiety, so it can respond to changes in viral enzymes and has a broader antiviral spectrum.

Further, ACV will be described as a comparison. In ACV, the sugar moiety has an acyclic structure, and the degree of freedom of the distance between the sugar hydroxyl group and the base is relatively high. However, because of the acyclic structure, in addition to the rotation around the carbon next to the hydroxyl group, the rotation around the second carbon counted from the hydroxyl group is also added, and the relationship between the base and the hydroxyl group becomes too complicated. There is. In other words, ACV suffers from the fact that the direction of the base and the carbon atom with a hydroxyl group do not always point in the same direction as nucleic acids (eg, thymidine) that make up DNA.
The number of viral enzymes that can interact is limited.

However, although the 3dGN of the present invention is relatively flexible, it does not have an acyclic structure, so that the structure of the base and the hydroxyl group is close to that of the nucleic acid (eg, thymidine) constituting DNA.

As described above, the 3dGN of the present invention has a special partial structure of 2 ′, 3 ′, 4′-trideoxyglucose in the molecule, so that it can be used as compared with conventional antiviral agents.
It is a new antiviral agent with a broad antiviral spectrum.

The antiviral agents of the present invention, 2 ', 3', 4'-trideoxygluconucleosides (3dGN), have a broad antiviral spectrum, but are retroviruses (especially AIDS virus) and helper viruses. Whistle (especially HSV-1, H
SV-2, etc.) show particularly high antiviral activity.

In addition, the antiviral agent of the present invention, 2 ', 3', 4'-
Trideoxygluconucleosides (3dGN) are all good antiviral agents, and among them, the following compounds exhibit high antiviral properties.

That is, the compounds are: a) 6-aminopurine-9-2 ', 3', 4'-trideoxyglucopyranoside, b) 6-hydroxypurine-9-2 ', 3', 4'-trideoxyglucopyranoside , C) purine-9-2 ', 3', 4'-trideoxyglucopyranoside, d) 2-amino-6-hydroxypurine-9-2 ',
3 ', 4'-trideoxyglucopyranoside, e) 6-fluoropurine-9-2', 3 ', 4'-trideoxyglucopyranoside, f) 6-chloropurine-9-2', 3 ', 4'- Trideoxyglucopyranoside, g) 2-amino-6-fluoropurine-9-2 ',
3 ', 4'-trideoxyglucopyranoside, h) 2-amino-6-chloropurine-9-2', 3 ',
4'-trideoxyglucopyranoside, and the like.

The 2,3,4-trideoxyglucopyranose derivative according to the present invention can be synthesized using inexpensively available ethyl 2-oxopentanecarboxylate as a raw material. For example, 1-
1 shows a method for synthesizing acetyl-6-benzoyl-2,3,4-trideoxyglucose (Scheme 1).

That is, after protecting the ketone portion of ethyl 2-oxopentanecarboxylate ( 1 ) as a ketal, the ester portion is reduced with a metal reagent, and further deprotected to obtain 2 -hydroxymethyl-pentanone ( 2 ). Further oxidation of compound 2 gives the corresponding lactone, 5-hydroxylmethyl-δ-pentanolactone ( 3 ). After protecting the alcohol part of compound 3 as benzoate and selectively reducing the lactone part to hemiacetal, and then converting it to acetate, the desired 1-acetyl-6-benzoyl-2,3,4
-Trideoxyglucose ( 4 ) can be synthesized.

Further, after converting the alcohol part of compound 3 to tertiary butyldimethylsilyl ether, the lactone part is reduced to hemiacetal, and further to acetate,
1-acetyl-6-tert-butyldimethylsilyl-
2,3,4-Trideoxyglucose ( 5 ) can be synthesized.

(Scheme 1) The 2,3,4-trideoxyglucopyranocose derivative synthesized as described above, a nucleobase obtained from inexpensive RNA, a synthetic nucleobase, or those obtained by chemically modifying them From the obtained nucleobase derivative, 2 ′, 3 ′, 4′-trideoxygluconucleoside (3dGN) according to the present invention can be easily synthesized.

For example, reacting 1-acetyl-6-benzoyl-2,3,4-trideoxyglucose with trimethylsilyl bromide to give 1-bromo-6-benzoyl-1,2,3,4-
After the tetradeoxyglucose is reacted with 6-chloropurine activated by sodium hydroxide, coupling occurs. When the benzoate is further deprotected, 6-chloropurine-9-2 ', 3' , 4'-
Trideoxyglucopyranoside is obtained.

As described above, according to the synthesis method of the present invention,
The antiviral agent according to the present invention can be synthesized from inexpensive raw materials by a simple technique.

〔Example〕

Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following examples are for illustrative purposes only, and are not intended to limit the scope of the present invention in any case.

(1) Production Example Production Example 1.1 Synthesis of 1-acetyl-6-benzoyl-2,3,4-trideoxyglucose (1) The synthesis of this compound was performed as follows, using ethyl 2-oxocyclopentanecarboxylate. Was used as a starting material and synthesized by the following methods (i) to (vii).

(I) ethyl 2-oxocyclopentanecarboxylate 4
6.8g (300mmol), ethylene glycol 93.1g (1.5mo
l), 5.17 g (30 mmol) of p-toluenesulfonic acid was placed in an eggplant flask containing benzene 1.5, refluxed, and reacted. The reaction was continued while removing water coming out of the reaction system, and refluxed for 20 hours. After completion of the reaction, the solvent was distilled off using a rotary evaporator, the residue was dissolved in ethyl acetate, and the mixture was washed twice with a saturated aqueous solution of sodium hydrogencarbonate and twice with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off to obtain 57.6 g (288 mmol) of ethyl 2,2-ethylenedioxycyclopentanecarboxylate (96%).

(Ii) 11.4 g (300 mmol) of LAH (lithium aluminum hydride) was added to 400 ml of distilled and dried anhydrous THF (tetrahydrofuran) under a nitrogen atmosphere, and L of THF was added.
Make an AH suspension and stir it with -20
Cooled to ° C. A solution of 50 g (250 mmol) of ethyl 2,2-ethylenedioxycyclopentanecarboxylate, synthesized in (i), in 200 ml of THF was slowly added dropwise to the LAH suspension under a nitrogen atmosphere to cause a reaction. After completion of the dropwise addition, stirring was continued for 1 hour. One hour later, the reaction was stopped by adding saturated ammonium chloride in small portions. After stirring was continued for a while, when bubbles were generated, ether and anhydrous sodium sulfate were further added for dehydration and extraction. After removing the solid content through the ether layer, the solvent was distilled off by a rotary evaporator, and the obtained residue was redissolved in ether. The ether solution was dried over anhydrous sodium sulfate, passed through a silica gel short column, and the solvent was distilled off using a rotary evaporator. The obtained residue was distilled (bp 150 to 160 ° C./18 mmHg) to give 1,1-ethylenedioxy-2-hydroxymethylcyclopropane 3
1.6 g (200 mmol) were obtained (80%).

(Iii) After dissolving 30.0 g (190 mmol) of 1,1-ethylenedioxy-2-hydroxymethylcyclopropane in 250 ml of acetone, several drops of water and 0.34 of paratoluenesulfonic acid were added.
Add 4 g (2 mmol) and stir at room temperature with a stirrer. Five minutes after the start of the reaction, the reaction was stopped by adding a saturated aqueous solution of sodium hydrogen carbonate, and after stirring for a while, ethyl ether and anhydrous sodium sulfate were added, and the mixture was stirred and extracted. The ether layer from which solids were removed by filtration was concentrated on a rotary evaporator, and the residue was distilled to give 2-hydroxymethylcyclopropanone (21.0 g).
(184 mmol) was obtained (97%).

(Iv) 20.0 g (175 mmol) of 2-hydroxymethylcyclopropanone was dissolved in 1.5 of anhydrous chloroform, and 36.2 g of mCPBA (metachloroperbenzoic acid) was dissolved with stirring at room temperature.
(210 mmol) and 17.64 g (210 mmol) of sodium bicarbonate were added simultaneously little by little. After the addition of mCPBA, the reaction was allowed to proceed for 5 hours while stirring at room temperature. After 5 hours, the reaction solution was passed through as it was to remove solids, the filtrate was concentrated on a rotary evaporator, and the residue was developed on a silica gel column chromatography using a mobile solvent of ether and methanol. I took it out. The fraction having an Rf value of 0.47 (ether / methanol = 3/1) was collected and concentrated, and 16.14 g of 5-hydroxymethyl-δ-pentanolactone (124 mmo) was collected.
l) was obtained (71%).

Colorless transparent oil Boiling point 120 ° C (0.5 mmHg) NMR spectrum (CHCl ₃ ): δ 1.2 to 2.2 (4H, m, C3 and C4-H) 2.2 to 2.75 (2H, m, C2-H) 3.25 (1H, s, 3.55 (2H, dd, C6-H) 4.1-4.7 (1H, m, C5-H) MS spectrum (FAB-MS; m / z) M + 1 131 Rf value (Silica Gel HF254; 0.47 (Et ₂ O / MeOH = 3/1) (v) 5-hydroxymethyl-δ-pentanolactone
15.0 g (115 mmol), 52.03 g (230 mmol) of benzoic anhydride,
1.4 g (11.5 mmol) of dimethylaminopyridine was dissolved in 400 ml of anhydrous pyridine and reacted by stirring at room temperature overnight.
After completion of the reaction, pyridine was distilled off using a rotary evaporator, and the residue was dissolved in ethyl acetate. The residue was washed twice with a 1N aqueous hydrochloric acid solution, a saturated aqueous sodium hydrogencarbonate solution, and a saturated aqueous ammonium chloride solution. Was. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. The residue was separated and purified by silica gel column chromatography (mobile layer; hexane / ether). Fractions having an Rf value of 0.2 (hexane / ether = 1/1) were collected and concentrated, and 25.3 g of 5-benzyloxymethyl-δ-pentanolactone (108
mmol) (94%).

(Vi) 23.4 g (100 mmol) of 5-benzyloxymethyl-δ-pentanolactone was dissolved in 200 ml of anhydrous THF under a nitrogen atmosphere, and cooled to 0 ° C with stirring. To this THF solution was added a 1.2 M disiamil borane THF solution (G. Zweifel et.a.
lJAm.Chem.Soc. 84, 190 (1962) ) was slowly added dropwise (250 ml) were reacted. After continuing stirring at room temperature for one day, 35 ml of water was added and the mixture was refluxed for 30 minutes. Thereafter, 70 ml of aqueous hydrogen peroxide was slowly added while cooling the reaction solution to 0 ° C. while adjusting the pH to 7 to 8 with a 3N aqueous sodium hydroxide solution. After completion of the dropwise addition, the mixture was stirred for a while and returned to room temperature. The solution was concentrated on a rotary evaporator to remove most of the THF,
Separation extraction was performed with chloroform. The chloroform solution thus obtained was dried over anhydrous calcium chloride, and then concentrated to dryness using a rotary evaporator. This residue was separated and purified by silica gel column chromatography (developing solvent; hexane / ether = 5/1). The fraction having an Rf value of 0.3 (hexane / ether = 1/1) was collected and concentrated.
2,3,4-trideoxyglucose-6-benzoate 18.
4 g (78.0 mmol) were obtained (78%).

(Vii) 16.0 g (67.7 mmol) of 2,3,4-trideoxyglucose-6-benzoate, 20.42 g (200 mmo) of acetic anhydride
l) 0.85 g (7.0 mmol) of dimethylaminopyridine is dissolved in 200 ml of anhydrous pyridine and reacted at room temperature for 5 hours.
After completion of the reaction, pyridine was distilled off using a rotary evaporator, the residue was dissolved in ethyl acetate, and separated twice with a 1N aqueous hydrochloric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous ammonium chloride solution. Washed. After drying the ethyl acetate layer with anhydrous sodium sulfate,
It was concentrated to dryness on a rotary evaporator. this,
Separation and purification were performed by silica gel column chromatography (developing solvent; hexane / ether = 8/1). Rf value is 0.59
The fraction (hexane / ether = 1/1) was collected and concentrated, and the target compound, 1-acetyl-6-benzoyl-2,3,4-trideoxyglucose, 16.2 g (58.2 mol)
(86%).

Colorless oil NMR spectrum _{(CHCl 3): δ 1.2~2.0 (} 6H, m, C2, C3 and C4-H) 2.1 (3H, s, CH 3 CO-) 3.7~4.45 (3H, m, C5 and C6- OH) 5.5~6.3 (1H, m, C5-H) 7.2~8.2 (5H, m, C 6 H 5 CO-) MS spectrum (FAB-MS; m / z ) M + 1 279 Rf value (Silica Gel HF254); 0.59 (hexame / Et ₂ O = 1/1) Preparation Example 2.6 Synthesis of 2-chloropurine-9-2 ′, 3 ′, 4′-trideoxyglucopyranoside (2) 1-acetyl-synthesized in Preparation Example 1. Under a nitrogen atmosphere, 1.43 g (5.13 mmol) of 6-benzoyl-2,3,4-trideoxyglucose was dissolved in 30 ml of anhydrous chloroform, and cooled to 0 ° C. with stirring. To this chloroform solution,
0.989 g (6.5 mmol) of trimethylsilyl bromide was slowly added dropwise. After completion of the dropwise addition, the temperature was returned to room temperature, and stirring was continued for 1 hour. After one hour, it was cooled again to -20 ° C.

After confirming that the temperature in the reaction system was −20 ° C., 6-chloro-9-trimethylsilylpurine derived from 6-chloropurine [6-chloropurine and N, O in acetonitrile
-Bis- (trimethylsilyl) -acetamide, mixed and reacted, and then the solvent was removed.] 0.793 g (5.
13 mmol) of chloroform solution (10 ml) was slowly added dropwise.
Reacted. After completion of the dropwise addition, the mixture was slowly raised to room temperature while stirring was continued, and stirring was continued at room temperature for 1 hour. 1
After an hour, the reaction was stopped by blowing into ice water, and extracted with chloroform. The chloroform layer was washed sequentially with a 0.5 N hydrochloric acid aqueous solution, a saturated aqueous solution of sodium hydrogen carbonate, and a saturated aqueous solution of ammonium chloride. The chloroform layer was dried over sodium sulfate, and then concentrated using a rotary evaporator. The obtained oily substance was separated and purified by silica gel column chromatography (hexane / ether = 1/5). The fraction having an Rf value of 0.4 (only ether) was collected and concentrated, and this was dried in vacuo (50 ° C., 1 hour)
1.20 g (3.21 mmol) of chloropurine-9-2 ', 3', 4'-trideoxyglucopyranoside-6'-benzoate were obtained as a glass (63%).

The thus obtained 6-chloropurine-9-2 ',
1.00 g (2.68 mmol) of 3 ', 4'-trideoxyglucopyranoside-6'-benzoate was dissolved in ammoniacal methanol (20% ammonia) and reacted at 20 ° C for 5 hours. After completion of the reaction, ammonia was distilled off at 10 ° C., and then methanol was distilled off with a rotary evaporator. The residue was separated and purified by silica gel column chromatography (chloroform / methanol = 9/1) and had an Rf value of 0.7.
The 6 fractions were collected and concentrated to give the target compound 6
0.583 g (2.17 mmol) of -chloropurine-9-2 ', 3', 4'-trideoxyglucopyranoside were obtained (81%).

Colorless transparent granular crystals Melting point 126 ° C NMR spectrum (DMSO-d6): δ 1.3 to 2.3 (6H, m, C2 ', C3' and C4'-H) 3.1 to 3.9 (3H, m, C5 'and C6'-H ) 4.6-4.9 (1H, t, C6'-OH disappeared by addition of D20) 5.6-6.0 (1H, dd, C1'-H) 8.4 (1H, s, C8-H) 8.7 (1H, s, C2-H) ) MS spectrum (FAB-MS; m / z) M + 1 269 Rf value (Silica Gel HF254); 0.76 (CHCl ₃ / MeOH = 9/1) Production Example 3.6-Aminopurine-9-2 ', 3', 4 ' -Synthesis of Trideoxyglucopyranoside (3) 6-chloropurine-9-2 ', 3', 4'-trideoxyglucopyranoside synthesized by the method shown in Production Example 2.
1.10 g (2.95 mmol) of 6'-benzoate was dissolved in ammoniacal methanol (20% ammonia) and placed in a sealed tube at 60 ° C.
For 10 hours. After completion of the reaction, ammonia was distilled off at 10 ° C., and then methanol was distilled off with a rotary evaporator. The residue was separated and purified by silica gel column chromatography (chloroform / methanol = 9/1), and the fraction having an Rf value of 0.31 was collected and concentrated to give the target compound, 6-aminopurine-9-2 ', 3. ′, 4′−
0.676 g (2.17 mmol) of trideoxyglucopyranoside was obtained (92%).

White needle crystals Melting point 192 ° C NMR spectrum (DMSO-d6): δ 1.3 to 2.4 (6H, m, C2 ', C3' and C4'-H) 3.2 to 4.0 (3H, m, C5 'and C6'-H) ) 4.5~4.9 (1H, t, C6' -OH D 2 O disappeared by addition) 5.55~5.9 (1H, dd, C1' -H) 7.25 (1H, s, -NH 2) 8.2 (1H, s, C8 -H) 8.4 (1H, s, C2-H) MS spectrum (FAB-MS; m / z ) M + 1 250 Rf value (Silica Gel HF254); 0.31 ( CHCl 3 / MeOH = 9/1) (2) anti-virus Testing Antiviral data for representative compounds according to the present invention are shown below. The compound numbers indicate the numbers of the above examples illustrating the preparation method in the examples of the present invention.

Test Example 1. The antiviral activity of the compounds represented by general formulas [I] and [II] of the present invention was determined by the test method of Rowe et al. (JWViolog
y, 42 1136 (1970)). Table 1 shows the antiviral results of representative compounds.

Virus: Moloney-murine leukemia virus Cell: SC-1 Test Example 2. The antiviral action of the compounds represented by the general formulas [I] and [II] of the present invention was tested using Rous meat virus (RSV).

Using primary cultured cells (Chick Embryo Fibrofast)
RSV infection was carried out for about 30 minutes. Then, a serially diluted sample was added, and after 4 to 7 days, it was determined by microscopy at which stage the transformation of the cells due to RSV infection was suppressed. The results are shown in Table 2.

As shown in Tables 1-2, the compounds of the present invention show excellent antiviral effects and have a broad antiviral spectrum, so that the compounds of the present invention are effective as therapeutic agents for viral diseases such as AIDS and herpes. It is clear that

〔The invention's effect〕

As described above, according to the present invention, a novel compound having an excellent antiviral action is provided. For example, it is extremely effective as a therapeutic drug for viral diseases such as AIDS and herpes.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07D 473/18 C07D 473/18 473/24 473/24 473/32 473/32 473/34 321 473/34 321 473/38 473 / 38 473/40 473/40 C07F 7/18 C07F 7/18 A // C07D 309/10 C07D 309/10 (58) Field surveyed (Int. Cl. ⁶ , DB name) C07D 473/00 C07D 473 / 06 C07D 473/16 C07D 473/18 C07D 473/24 C07D 473/32 C07D 473/34 C07D 473/38 C07D 473/40 C07F 7/18 C07D 405/04 A61K 31/52 C07D 309/10

Claims (13)

(57) [Claims] 1. A compound of the general formula [I] (Wherein R ₁ is a hydrogen atom, a hydroxyl group, an amino group, an alkyl group,
A halogen atom, an alkoxy group, or a mercapto group, and R ₂ and R ₃ are each a hydrogen atom or an amino group). 2. 6-aminopurine-9-2 ', 3', 4'-trideoxyglucopyranoside, 6-hydroxypurine-9-2 ', 3', 4'-trideoxyglucopyranoside, purine-9-2 ', 3', 4'-Trideoxyglucopyranoside, 2-amino-6-hydroxypurine-9-2 ', 3', 4 '
-Trideoxyglucopyranoside, 6-fluoropurine-9-2 ', 3', 4'-trideoxyglucopyranoside, 6-chloropurine-9-2 ', 3', 4'-trideoxyglucopyranoside, 2-amino-6 -Fluoropurine-9-2 ', 3', 4'-
The compound according to claim 1, which is selected from trideoxyglucopyranoside, 2-amino-6-chloropurine-9-2 ', 3', 4'-trideoxyglucopyranoside. 3. A compound of the general formula [III] (Where Ra is a hydrogen atom or a protecting group for an alcohol selected from acetyl, benzoyl and esters having up to C10 carbon atoms, or benzyl, tetrahydropyranyl, ethoxyethyl ether, trityl, t-butyl) A compound represented by any one of a dimethylsilyl group and an alcohol-protecting group selected from ethers having up to C20 carbon atoms, and Rb represents a hydrogen atom or an acetyl group. (4) 1-acetyl-6-benzoyl-2,3,4-
Trideoxyglucose, 1-acetyl-6- (t-butyldimethylsilyl) -2,
The compound according to claim 3, wherein the compound is selected from 3,4-trideoxyglucose. 5. A compound of the general formula [IV] (Wherein R ₁ is a hydrogen atom, a hydroxyl group, an amino group, an alkyl group,
A halogen atom, an alkoxy group, or a mercapto group, and R ₂ and R ₃ are each a hydrogen atom or an amino group); and a general formula [III] (Where Ra is a hydrogen atom or a protecting group for an alcohol selected from acetyl, benzoyl and esters having up to C10 carbon atoms, or benzyl, tetrahydropyranyl, ethoxyethyl ether, trityl, t-butyl) A compound represented by a dimethylsilyl group or an alcohol-protecting group selected from ethers having up to C20 carbon atoms, and Rb represents a hydrogen atom or an acetyl group (hereinafter referred to as 2,3,4 And a compound represented by the general formula [I] (hereinafter referred to as 2 ′, 3 ′, or 2 ′) obtained by fusing an appropriate coupling reagent and deprotecting Ra. 4′-trideoxyglucopurine nucleosides). (Wherein R ₁ , R ₂ , and R ₃ are the same as in general formula [IV]) 6. The coupling reagent according to claim 5, wherein
A process for producing a compound represented by the general formula [I] (hereinafter, referred to as 2 ', 3', 4'-trideoxygluconucleosides) using sodium hydride and trimethylsilyl bromide. 7. The coupling reagent according to claim 5, wherein
A process for producing 2 ', 3', 4'-trideoxygluconucleosides, comprising using a silylating agent such as trimethylsilyl chloride, N, O-bis- (trimethylsilyl) -acetamide and trimethylsilyl bromide. 8. The coupling reagent according to claim 5, wherein
A process for producing 2 ', 3', 4'-trideoxygluconucleosides, comprising using a Lewis acid such as ethylaluminum dichloride. 9. An antiviral agent comprising at least one of the 2 ', 3', 4'-trideoxygluconucleosides represented by the general formula [I] according to claim 1 as an active ingredient. 10. An antiretroviral agent comprising at least one of the 2 ', 3', 4'-trideoxygluconucleosides represented by the general formula [I] according to claim 1 as an active ingredient. 11. An anti-herpes agent comprising at least one of the 2 ', 3', 4'-trideoxygluconucleosides represented by the general formula [I] according to claim 1 as an active ingredient. 12. An anti-AIDS virus agent comprising as an active ingredient at least one of the 2 ', 3', 4'-trideoxygluconucleosides represented by the general formula [I] according to claim 1. 13. An experiment used for genetic engineering, comprising at least one of the 2 ', 3', 4'-trideoxygluconucleosides represented by the general formula [I] according to claim 1 as an active ingredient. Pharmaceuticals and laboratory reagents.