WO1986004056A1 - Propanol derivatives - Google Patents
Propanol derivatives Download PDFInfo
- Publication number
- WO1986004056A1 WO1986004056A1 PCT/DK1986/000005 DK8600005W WO8604056A1 WO 1986004056 A1 WO1986004056 A1 WO 1986004056A1 DK 8600005 W DK8600005 W DK 8600005W WO 8604056 A1 WO8604056 A1 WO 8604056A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compounds
- formula
- group
- bromo
- bromine
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/36—Halogenated alcohols the halogen not being fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Definitions
- the present invention relates to novel alkylating reagents useful as starting materials in organic synthesis .
- Multifunctional compounds are of great value as starting materials in organic synthesis .
- Most of the simple, low-molecular weight compounds in this category are well known in the literature.
- a number of possible isomers of alcohols with the molecular formula C 4 HQB ⁇ 0 have already been described (S . A . Pogorshelski, Chem. Zentralbl . , 7, (1905) , p 668) .
- One object of the present invention is to provide novel propanol derivatives useful as starting materials in organic synthesis.
- Another object of the present invention is to provide a method for preparing the propanol derivatives of the invention .
- the invention relates to propanol derivatives of the formula I
- X is a leaving group
- R is H or a protecting group
- R « is H
- R « is a group -CH-Y wherein Y is a leaving group
- R « and R., together form CH ⁇ .
- the term "leaving group" for X or Y de ⁇ signates any of the groups used in the art that are easily split off when the carbon atom, to which they are attached, is subjected to nucleophilic attack .
- Typical examples of leaving groups are halogens such as chlorine, bromine, and iodine, in particular bromine; p-toluene sulphonyl, methyl sulphonyl , ester functions such as C, nalkyl carbonyloxy, e. g . methyl carbonyloxy, ethyl carbonyloxy, propyl carbonyloxy, etc. , and aryl ester functions such as phenyl carbonyl ⁇ oxy, wherein the phenyl group may optionally be substituted with electron-withdrawing groups such as nitro or fluoro.
- protecting group designates any group that on the one hand is able to prevent the oxygen atom, to which it is attached, from taking part in the substitution or elimination reactions, and on the other hand may be removed easily.
- protecting groups are enol ethers (formed with ketones having ⁇ -protons) ; acyl such as C, g al kyl carbonyl, e. g . acetyl, propionyl, butyryl etc.
- C, fi alkyl used above in connection with ester functions may designate such groups as methyl , ethyl , propyl , i-propyl, n-butyl , i-butyl , tert. butyl , pentyl , hexyl , and octyl .
- I n the subgroup of compounds of the formula I wherein R is H , it is preferred that X and Y are identical , in particular selected from the leaving groups described above, especially halogens such as chlorine, bromine, or iodine, bromine being especially preferred .
- substituent R is H since such compounds may act as nucleophiles .
- X is selected from the leaving groups described above, in particu lar halogens such as chlorine, bromine, and iodine, bromine being especially preferred .
- An especially preferred compound is 3-bromo-2-bromomethylpropan- 1 -ol .
- the compounds of the formula I possess good properties as multi ⁇ functional reagents .
- R is H
- the compounds in which R ⁇ is a group -CH ⁇ Y can be reacted with a variety of nucleophilic reagents depending on the properties of the leaving groups X and Y. I n this connection , mercapto ions are particularly interesting nucleophilic reagents .
- This activation makes it possible for such nucleophilic reagents as ketone or ester enolates, amines or alcohols to react easily with the compound of the formula I .
- the allylic alcohol derivatives formed after such alkylation reactions are useful as starting compounds in a Sharpless-epoxidation (cf. e. g . K. B . Sharpless, Org. Synth . , 63) ) whereby, th rough reaction with tert. butylhydroperoxide and e. g . Ti [OCH (CH «) «] 4 and a 2R, 3R-tartrate, optically active compounds may be formed in high yield .
- a particularly interesting use of the compounds of the formula I concerns the preparation of synthetic carbohydrate receptors such as those described in Applicant's copending application entitled “Gly- cosidic Derivatives” filed on the same date as the present application .
- the compounds, the group R, in the formula I above is a receptor- active carbohydrate moiety, and the group X and optionally Y are replaced with various functional groups such as lipids , carriers , etc. Syntheses of this type are exemplified in Example 4 and 5.
- the receptor-active carbohydrate moiety may be introduced into compounds of the formula I by reacting a compound of the formula I , wherein R, is H , with a derivative of the appropiate receptor-active carbohydrate having a leaving group at the reducing end of the carbohydrate. In this way, the receptor-active carbohydrate moiety is introduced in the place of the group R, in the formula I above.
- various groups such as lipid groups, carriers etc. may be introduced in the place of the group X in the formula I above th rough reaction with appropiate nucleophilic derivatives of the groups to be introduced .
- the sulfides may optionally be oxidized to sulfoxides or sulfones .
- the present invention also relates to a process for preparing the propanol derivatives of the formula I defined above.
- a process a) for preparing compounds in which R ⁇ is H, and R-. is -CH ⁇ Y comprises reducing the corresponding acid of the formula I I CH 2 Y
- the reduction may be performed by means of a wide variety of reducing agents such as NaBH , in water or protic or aprotic, polar or non-polar organic solvents such as methanol , ethanol , isopropanol , diglyme, benzene, toluene, ether, tetrahydrofuran, or 1 ,2-dimethoxy- ethane or by means of reducing agents such as diborane or LiAIH , in aprotic, polar or non-polar organic solvents such as benzene, toluene, ether, tetrahydrofuran, or 1 ,2-dimethoxyethane.
- reducing agents such as NaBH
- polar or non-polar organic solvents such as methanol , ethanol , isopropanol , diglyme, benzene, toluene, ether, tetrahydrofuran, or 1 ,2-dimethoxy- ethane
- the reduction may also be carried out by reducing the corresponding acid chloride or an ester by treatment with an alkali metal such as potassium, lithium, or sodium in liquid ammonia, by treatment with a hydride as mentioned above, or by treatment with a reducing complex such as Red-AI (Na-bis (2-methoxyethoxy)AL) , the solvent being one of the previously mentioned solvents .
- the acid chloride or ester may also be subjected to a first reduction to the aldehyde, using hydrogen catalyzed by Pd/BaSO , , followed by a second reduction to the alcohol , using NaBH , .
- the reaction may be carried out at temperatures in the range from -78°C to + 150°C, normally from 0°C to 50°C such as room temperature, for a period of 0.1 -48 hours, normally 8-24 hours such as 16 hours .
- the halo- genating agent used may be any of the agents commonly used in the art such as thionyl chloride, phosphorous tribromide, or phosphorous pentabromide in e. g . pyridine, or triphenyi phosphine in CCL or triphenyi phosphine in CBr ..
- the reaction may be carried out at temperatu res in the range from -78°C to + 200°C, normally from 0°C to 100°C such as the refluxing temperatu re of the solvent used , for 0.1 - 100 hours , normally 8-24 hours such as 16 hours .
- the preparation of iodides may be carried out by reacting the chlorides or bromides obtained above or e . g . the tosylate or the methane sulphonate with sodium iodide in refluxing acetone.
- the diol of formula I I I may be prepared by protecting 2-hydroxy- methyl-1 ,3-propandiol with an acetal group .
- an acetal group may be a benzylidene acetal group or an acetal group derived from a ketone such as cyclohexanone.
- a benzyliden acetal group may be established by reacting the triol with benzaldehyde and acid, or with ⁇ , ⁇ -dimethoxy toluene and acid .
- the acetal protected triol is then protected with R, after which the acetal function is removed by reaction with an acid such as hydrochloric acid .
- a process c) for the preparation of compounds of the formula I wherein R ⁇ and F together form CH « comprises subjecting a compound of the formula I wherein R- is H, and R ⁇ is -CH-Y to an elimination reaction .
- Such an elimination may suitably be carried out by treatment with a base such as an al kali metal hydroxide or carbonate, diazabicycloundecane, or diazabicyclononane.
- a base such as an al kali metal hydroxide or carbonate, diazabicycloundecane, or diazabicyclononane.
- al kali metal hydroxides and carbonates are sodium hydroxide, potassium hydroxide, lithium hydroxide, cesi um hydroxide, sodium carbonate, potassium carbonate, lithium carbonate and cesium carbonate, the treatment being carried out in e. g . dimethyl formamide, ethanol , or isopropanol .
- Treatment with the non-hydrophilic diaza bases may take place in aprotic solvents such ethyl acetate, methylene chloride, carbon tetrachloride, benzene, toluene, or ether.
- the reaction may take place at a temperature in the range from -78°C to + 150°C, normally from 0°C to 100°C such as room temperature, for a period of 0. 1 -24 hours, normally 8-24 hou rs such as 16 hours .
- the process c) may be carried out as part of the use for reacting with a nucleophile immediately before addition of the nucleophile, e. g. a thiole, an alcohol or an amine.
- the reaction is a Wittig- reaction and is usually carried out in aprotic solvents such as ether or tetra ⁇ hydrofuran at temperatu res in the range from -78°C to + 150°C, normally from 0°C to 100°C such as the reflu xing temperatu re of the solvent used, for a period of 0. 1'-72 hou rs, normally 8-24 hou rs such as 16 hours .
- the phosphorane compound is usually prepared from methyltriphenylphosphonium bromide by treatment with a strong base such as butyllithium .
- the compounds of the formula I in which R ⁇ is H , and X and Y are p-toluene sulphonyl, methane sulphonyl, C, perhapsalkyl carbonyloxy, or phenyl carbonyloxy may be prepared by a process e) which comprises reacting the diol of formula I I I defined above with p-toluene sulphonyl chloride, methane sulphonyl chloride, a C, _oalkyl carbonyl chloride, or a phenyl carbonyl chloride in a polar solvent such as pyridine at temperatu res in the range from -78°C to + I50°C, normally from 0°C to 100°C such as the refluxing temperatu re of the solvent used, for a period of 0. 1 -24 hou rs, normally 8-24 hours such as 16 hours .
- a polar solvent such as pyridine
- the acetylated glycolipid (0.2 mmol) was dissolved in dichloromethage (15 ml) and methanolic sodium methoxide (10 ml; prepared by dis ⁇ solving ca. 1 mg of sodium in methanol) was added.
- the reaction was monitored by TLC (chloroform: methanol :water, 65:35:10). In some cases, a precipitate was formed towards the end of the reaction.
- One drop of acetic acid was added and the reaction mixture was concentra ⁇ ted, suspended in water (10 ml) and freeze-dried to give a quantita ⁇ tive yield of the unprotected glycolipid, contaminated with a small amount of sodium acetate (ca. 1% w/w) .
- the following compounds were prepared:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pistons, Piston Rings, And Cylinders (AREA)
- Saccharide Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61500823A JPH0778028B2 (en) | 1985-01-14 | 1986-01-13 | Propanol derivative |
DE8686900751T DE3680725D1 (en) | 1985-01-14 | 1986-01-13 | Propanolabkoemmlinge. |
AT86900751T ATE65986T1 (en) | 1985-01-14 | 1986-01-13 | PROPANONE COMBATIVES. |
DK439286A DK439286D0 (en) | 1985-01-14 | 1986-09-12 | PROPANOL DERIVATIVES |
NO863647A NO166408C (en) | 1985-01-14 | 1986-09-12 | Propanol. |
FI863701A FI88287C (en) | 1985-01-14 | 1986-09-12 | PROPANOLDERIVAT |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK17785A DK17785D0 (en) | 1985-01-14 | 1985-01-14 | PROPANOL DERIVATIVES |
DK177/85 | 1985-01-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1986004056A1 true WO1986004056A1 (en) | 1986-07-17 |
Family
ID=8090639
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/DK1986/000005 WO1986004056A1 (en) | 1985-01-14 | 1986-01-13 | Propanol derivatives |
Country Status (14)
Country | Link |
---|---|
US (1) | US4933510A (en) |
EP (1) | EP0210203B1 (en) |
JP (1) | JPH0778028B2 (en) |
CN (1) | CN1019387B (en) |
AT (1) | ATE65986T1 (en) |
AU (1) | AU588570B2 (en) |
CA (1) | CA1292002C (en) |
DE (1) | DE3680725D1 (en) |
DK (2) | DK17785D0 (en) |
FI (1) | FI88287C (en) |
IE (1) | IE58795B1 (en) |
IL (1) | IL77601A (en) |
NO (1) | NO166408C (en) |
WO (1) | WO1986004056A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4996345A (en) * | 1989-06-21 | 1991-02-26 | Pfizer Inc. | Difluoroketones from difluoroacylsilanes |
WO1998005634A1 (en) * | 1996-08-02 | 1998-02-12 | Kaneka Corporation | Sulfonic ester derivatives, process for preparing the same, and use thereof |
CN102952017A (en) * | 2011-08-24 | 2013-03-06 | 湖北保乐制药有限公司 | Preparation method of 2-acetylchloromethoxy-1,3-dichloropropane |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2252706A (en) * | 1938-10-20 | 1941-08-19 | Squibb & Sons Inc | Haloalkyl polyacyl glycosides |
US3856535A (en) * | 1973-12-06 | 1974-12-24 | Ici America Inc | Emulsifiable haloalkyl phosphate blend for aqueous textile flame-retardant treatments |
US4016200A (en) * | 1974-03-12 | 1977-04-05 | Mitsubishi Chemical Industries Ltd. | Process for preparing carboxylic acid esters from toluene and xylene |
FR2508032A1 (en) * | 1981-06-17 | 1982-12-24 | Delalande Sa | 3-Amino-2-aryloxy-methyl-1-propanol derivs. - are used to treat cardiovascular troubles, esp. angina esp 3-tri:methoxy-cinnamoyl-piperazino- 2-1,4-benzodioxan-5-yl-oxy-methyl cpds. |
EP0098252A2 (en) * | 1982-06-23 | 1984-01-11 | Biocarb Ab | New and novel glycosides, glycoconjugates and processes for their preparation |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK17685D0 (en) * | 1985-01-14 | 1985-01-14 | Hans Goeran Magnusson | glycoside |
-
1985
- 1985-01-14 DK DK17785A patent/DK17785D0/en not_active Application Discontinuation
-
1986
- 1986-01-10 IE IE7686A patent/IE58795B1/en not_active IP Right Cessation
- 1986-01-13 DE DE8686900751T patent/DE3680725D1/en not_active Expired - Fee Related
- 1986-01-13 CN CN86100170A patent/CN1019387B/en not_active Expired
- 1986-01-13 AU AU53516/86A patent/AU588570B2/en not_active Ceased
- 1986-01-13 JP JP61500823A patent/JPH0778028B2/en not_active Expired - Lifetime
- 1986-01-13 AT AT86900751T patent/ATE65986T1/en active
- 1986-01-13 WO PCT/DK1986/000005 patent/WO1986004056A1/en active IP Right Grant
- 1986-01-13 EP EP86900751A patent/EP0210203B1/en not_active Expired - Lifetime
- 1986-01-14 CA CA000499565A patent/CA1292002C/en not_active Expired - Fee Related
- 1986-01-14 IL IL77601A patent/IL77601A/en not_active IP Right Cessation
- 1986-09-12 FI FI863701A patent/FI88287C/en not_active IP Right Cessation
- 1986-09-12 NO NO863647A patent/NO166408C/en unknown
- 1986-09-12 DK DK439286A patent/DK439286D0/en not_active Application Discontinuation
-
1989
- 1989-03-13 US US07/323,245 patent/US4933510A/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2252706A (en) * | 1938-10-20 | 1941-08-19 | Squibb & Sons Inc | Haloalkyl polyacyl glycosides |
US3856535A (en) * | 1973-12-06 | 1974-12-24 | Ici America Inc | Emulsifiable haloalkyl phosphate blend for aqueous textile flame-retardant treatments |
US4016200A (en) * | 1974-03-12 | 1977-04-05 | Mitsubishi Chemical Industries Ltd. | Process for preparing carboxylic acid esters from toluene and xylene |
FR2508032A1 (en) * | 1981-06-17 | 1982-12-24 | Delalande Sa | 3-Amino-2-aryloxy-methyl-1-propanol derivs. - are used to treat cardiovascular troubles, esp. angina esp 3-tri:methoxy-cinnamoyl-piperazino- 2-1,4-benzodioxan-5-yl-oxy-methyl cpds. |
EP0098252A2 (en) * | 1982-06-23 | 1984-01-11 | Biocarb Ab | New and novel glycosides, glycoconjugates and processes for their preparation |
Non-Patent Citations (2)
Title |
---|
Angewandte Chemie Vol 78 (1) p 116 (1966) & Chemical Abstracts Vol 64, column 12566 b (1966) * |
Chemical Abstract Vol 46, column 380 f (1952) * |
Also Published As
Publication number | Publication date |
---|---|
CN1019387B (en) | 1992-12-09 |
AU5351686A (en) | 1986-07-29 |
NO863647D0 (en) | 1986-09-12 |
JPS62502259A (en) | 1987-09-03 |
CN86100170A (en) | 1986-12-17 |
FI88287C (en) | 1993-04-26 |
EP0210203B1 (en) | 1991-08-07 |
AU588570B2 (en) | 1989-09-21 |
IE58795B1 (en) | 1993-11-17 |
US4933510A (en) | 1990-06-12 |
NO166408B (en) | 1991-04-08 |
IE860076L (en) | 1986-07-14 |
DK439286A (en) | 1986-09-12 |
IL77601A (en) | 1991-11-21 |
CA1292002C (en) | 1991-11-12 |
ATE65986T1 (en) | 1991-08-15 |
FI863701A0 (en) | 1986-09-12 |
DE3680725D1 (en) | 1991-09-12 |
FI88287B (en) | 1993-01-15 |
EP0210203A1 (en) | 1987-02-04 |
DK17785D0 (en) | 1985-01-14 |
NO166408C (en) | 1991-07-17 |
JPH0778028B2 (en) | 1995-08-23 |
DK439286D0 (en) | 1986-09-12 |
FI863701A (en) | 1986-09-12 |
NO863647L (en) | 1986-09-12 |
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