WO1995033845A1 - Procede de production d'un compose d'alcool propargylique optiquement actif - Google Patents
Procede de production d'un compose d'alcool propargylique optiquement actif Download PDFInfo
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- WO1995033845A1 WO1995033845A1 PCT/JP1995/001064 JP9501064W WO9533845A1 WO 1995033845 A1 WO1995033845 A1 WO 1995033845A1 JP 9501064 W JP9501064 W JP 9501064W WO 9533845 A1 WO9533845 A1 WO 9533845A1
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- Prior art keywords
- group
- carbon atoms
- formula
- optically active
- alkyl group
- Prior art date
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- -1 propargyl alcohol compound Chemical class 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 102000004190 Enzymes Human genes 0.000 claims abstract description 14
- 108090000790 Enzymes Proteins 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 230000003287 optical effect Effects 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 244000005700 microbiome Species 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical class OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZOYAOIBMVRUEDS-VIFPVBQESA-N C#C[C@@H](COC1CCCCC1)O Chemical compound C#C[C@@H](COC1CCCCC1)O ZOYAOIBMVRUEDS-VIFPVBQESA-N 0.000 description 2
- YIMCOYJWZNSJML-JTQLQIEISA-N CCCCCCOC[C@H](C#C)O Chemical compound CCCCCCOC[C@H](C#C)O YIMCOYJWZNSJML-JTQLQIEISA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical compound O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZOYAOIBMVRUEDS-UHFFFAOYSA-N C(#C)C(COC1CCCCC1)O Chemical compound C(#C)C(COC1CCCCC1)O ZOYAOIBMVRUEDS-UHFFFAOYSA-N 0.000 description 1
- IGTGDTFNPFTLFY-LLVKDONJSA-N CC(=O)O[C@@H](COC1CCCCC1)C#C Chemical compound CC(=O)O[C@@H](COC1CCCCC1)C#C IGTGDTFNPFTLFY-LLVKDONJSA-N 0.000 description 1
- YIMCOYJWZNSJML-UHFFFAOYSA-N CCCCCCOCC(C#C)O Chemical compound CCCCCCOCC(C#C)O YIMCOYJWZNSJML-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- LMJIECGJNREYCB-UHFFFAOYSA-N but-3-ynoxybenzene Chemical compound C#CCCOC1=CC=CC=C1 LMJIECGJNREYCB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- QVQPFHVJHZPVDM-UHFFFAOYSA-N prop-1-en-2-yl benzoate Chemical compound CC(=C)OC(=O)C1=CC=CC=C1 QVQPFHVJHZPVDM-UHFFFAOYSA-N 0.000 description 1
- NLDFTWSUPLJCQD-UHFFFAOYSA-N prop-1-en-2-yl propanoate Chemical compound CCC(=O)OC(C)=C NLDFTWSUPLJCQD-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
Definitions
- the present invention relates to an optically active propargyl alcohol compound and a method for producing an acylated product thereof.
- optically active propargyl alcohol compounds and their acylated compounds are important as synthetic intermediates for various biologically active substances.
- methods for producing optically active propargyl alcohol include (1) a method of optically reducing ketones (Gooding OW et al., J. Org. Chem., Vol. 58, p. 368, page 1). (2) Method for synthesis from 2,3-0-isopropylidene-slate (Niidas P. et al., Eesti NSV Tead Akad. Toim., Keem., Vol. 38 ( 4), pp. 285-6, 1989).
- An object of the present invention is to provide a simpler method for producing an optically active propargyl alcohol compound having excellent optical purity and an acylated product thereof. Disclosure of the invention
- the present inventors have conducted intensive studies for the purpose of solving the above-mentioned problems, and as a result, by stereoselectively acylating a racemic propargyl alcohol compound using an enzyme, a high purity and a high yield of the optically active compound are obtained.
- the present inventors have found that a propargyl alcohol compound can be produced, and have completed the present invention.
- R 1 and R 2 each represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
- R 3 represents a phenyl group, a ⁇ alkynol group having 1 to 5 carbon atoms, a halogen atom, a trifluoromethyl group
- R 4 represents an alkyl group having 1 to 10 carbon atoms
- the * symbol indicates that the compound is optically active.
- a Lugyl alcohol compound is reacted in the presence of an enzyme with an acylating agent represented by the formula R 4 COOR (where R 4 has the same meaning as described above, and R represents any alkynole or alkenyl group).
- R 4 has the same meaning as described above, and R represents any alkynole or alkenyl group.
- a method for producing an optically active 0-acylpropargyl alcohol compound represented by the formula (1) characterized by comprising:
- Another aspect of the present invention provides a method of formula (3), comprising separating an optically active 0-acylpropargyl alcohol compound of the formula (1) from the reaction solution after the above reaction, and hydrolyzing the compound.
- Another aspect of the present invention is to provide an optically active compound, comprising separating an optically active pergyl alcohol compound having a steric configuration different from that of the compound of the formula (3) from the reaction solution after the reaction. This is a method for producing a propargyl alcohol compound.
- the halogen atom is a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- the alkyl group having 1 to 3 carbon atoms is a chain or branched alkyl group, for example, a methyl group, an ethyl group, and an isopropyl group. Of these, a methyl group or an ethyl group is preferred.
- the alkyl group having 1 to 5 carbon atoms is a chain or branched alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, and an isopentyl group. .
- An alkyl group having 1 to 8 carbon atoms is a chain or branched alkyl group, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, and the like.
- An alkyl group having 1 to 10 carbon atoms is a chain or branched alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, a Examples include a sopentyl group, a hexyl group, an isohexyl group, a heptyl group, and an isoheptyl group. Among them, preferred are a methyl group, an ethyl group, a propyl group, an isopropyl group and a butyl group.
- Examples of the cycloalkyl group having 5 to 8 carbon atoms include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and the like.
- the arbitrary alkyl group or alkenyl group represented by R may be any group which does not affect the reaction at all, for example, a methyl group, an ethyl group, a propynole group, an isopropyl group, a butyl group Group, isobutyl group, pentyl group, isopentyl group, hexyl group, isohexyl group, heptyl group, isoheptyl group, vinyl group, aryl group, 1-propenyl group, 2-buteninole group, isopropyl group And so on.
- the enzyme used in the present invention refers to an optically active 0-acylpropargyl alcohol compound of the formula (1) formed from a (RS) -proparginole alcohol compound of the formula (2)
- An enzyme having the activity of causing Preferred is an enzyme produced by a microorganism belonging to the genus Pseudomonas, and more preferred is lipase PS (Amano Pharmaceutical).
- vinyl acetate, isopropenylpropionate, or isopropenylbenzoate can be used as the acylating agent, and is preferably isoprobenyl acetate.
- Prono of the above formula (2) which is a raw material.
- the racemic form of lugyl alcohol can be easily obtained, for example, by reacting the corresponding aldehyde form (4) with the acetylene Grignard reagent (5) as shown below (in the reaction formula, RR 2 and R 3 are as defined above, and X represents a bromo or chloro atom.
- reaction with isopropenyl acetate is carried out by adding 0.1 to 50 times by weight of the enzyme and 1 to 50 parts by weight of the racemic propargyl alcohol of the formula (2).
- the reaction is carried out in an inert solvent at 0 to 50 ° C. using 100 equivalents.
- the inert solvent include methylene chloride, toluene, ether, t-butyl methyl ether and the like.
- the reaction time varies considerably depending on the substrate, the reaction temperature and the amount of the enzyme, and varies from as little as one hour to several days, and is it possible to obtain the preferred isomer as an acetyl form? It is desirable to adjust as appropriate depending on whether the alcohol is obtained as unreacted alcohol. In the former case, it is preferable to keep the reaction rate at 50% or less, and in the latter case, conversely, when the reaction rate is raised to 50% or more, a compound with good optical purity can be obtained.
- the obtained alcohol form was prepared according to the method of Niidas P. et al. (Eesti NSV Tead Akad. Toim., Keem., Volume 38 (4 ), Pp. 285-6, 1989), and confirmed to be S-form.
- Example 2 The same operation as in (1) of Example 2 was performed using (3RS) —3-hydroxy-4,4-dimethyl-4-pentoxy-1-butyne obtained by the same method as in Example 1.
- the present invention is useful as a simpler method for producing an optically active propargyl alcohol compound having a higher optical purity and an acylated product thereof.
- optically active propargyl alcohol compounds and their acylated compounds are important as intermediates for the synthesis of various physiologically active substances, but are particularly important as intermediates for the synthesis of the ⁇ side chain of prostaglandin derivatives useful as pharmaceuticals. is there.
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Abstract
L'invention concerne un procédé permettant d'obtenir, de façon stéréosélective, un composé d'alcool O-acylpropargylique optiquement actif, représenté par la formule générale (2) (dans laquelle R1 et R2 représentent chacun hydrogène ou alkyle C¿1?-C3; R?3¿ représente phényle pouvant être substitué par alkyle C¿1?-C5, halogéno ou trifluorométhyle en une position arbitraire du noyau, alkyle C1-C8 ou cycloalkyle C5-C8; R?4¿ représente alkyle C¿1?-C10 ou phényle pouvant être substitué par phényle ou halogéno en une position arbitraire du noyau; et l'astérisque représente l'activité optique), ledit procédé consistant à faire réagir un composé d'alcool (RS)-propargylique représenté par la formule générale (1) (dans laquelle R?1, R2 et R3¿ correspondent à la définition donnée ci-dessus) avec un agent d'acylation correspondant à la formule R4COOR (où R4 correspond à la définition donnée ci-dessus et R représente un alkyle ou un alcényle arbitraire) en présence d'une enzyme. L'invention concerne également un procédé permettant d'obtenir un composé d'alcool propargylique optiquement actif soit par hydrolyse du composé O-acylique mentionné ci-dessus ou à partir de la solution résultant de la réaction d'acylation susmentionnée.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU25752/95A AU2575295A (en) | 1994-06-02 | 1995-05-31 | Process for producing optically active propargyl alcohol compound |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12145994 | 1994-06-02 | ||
| JP6/121459 | 1994-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1995033845A1 true WO1995033845A1 (fr) | 1995-12-14 |
Family
ID=14811664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1995/001064 WO1995033845A1 (fr) | 1994-06-02 | 1995-05-31 | Procede de production d'un compose d'alcool propargylique optiquement actif |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2575295A (fr) |
| WO (1) | WO1995033845A1 (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000061777A1 (fr) * | 1999-04-12 | 2000-10-19 | Chirotech Technology Limited | Procede de preparation de precurseurs de la prostaglandine |
| US6214611B1 (en) | 1999-04-12 | 2001-04-10 | Chirotech Technology Limited | Process for the preparation of prostaglandin precursors |
| WO2006076565A3 (fr) * | 2005-01-14 | 2006-12-07 | Schering Corp | Preparation d'alcool propargylique chiral et d'intermediaires d'ester d'analogues d'himbacine |
| US7897795B2 (en) | 2008-04-09 | 2011-03-01 | Scinopharm Taiwan Ltd. | Process for the preparation of prostaglandin analogues and intermediates thereof |
| CN103917665A (zh) * | 2011-11-09 | 2014-07-09 | 纳幕尔杜邦公司 | 用于沙门氏菌检测的序列和它们的用法 |
| WO2020255164A1 (fr) * | 2019-06-21 | 2020-12-24 | Council Of Scientific And Industrial Research | Procédé chimio-enzymatique pour la préparation d'alcool homopropargylique |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01171497A (ja) * | 1987-12-26 | 1989-07-06 | Lion Corp | ラセミアルコールの光学分割法 |
| JPH02262536A (ja) * | 1989-04-01 | 1990-10-25 | Arakawa Chem Ind Co Ltd | 光学活性化合物およびその製法 |
| JPH03210194A (ja) * | 1990-01-11 | 1991-09-13 | Konica Corp | 多層分析素子 |
-
1995
- 1995-05-31 WO PCT/JP1995/001064 patent/WO1995033845A1/fr active Application Filing
- 1995-05-31 AU AU25752/95A patent/AU2575295A/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01171497A (ja) * | 1987-12-26 | 1989-07-06 | Lion Corp | ラセミアルコールの光学分割法 |
| JPH02262536A (ja) * | 1989-04-01 | 1990-10-25 | Arakawa Chem Ind Co Ltd | 光学活性化合物およびその製法 |
| JPH03210194A (ja) * | 1990-01-11 | 1991-09-13 | Konica Corp | 多層分析素子 |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000061777A1 (fr) * | 1999-04-12 | 2000-10-19 | Chirotech Technology Limited | Procede de preparation de precurseurs de la prostaglandine |
| US6214611B1 (en) | 1999-04-12 | 2001-04-10 | Chirotech Technology Limited | Process for the preparation of prostaglandin precursors |
| JP2002541816A (ja) * | 1999-04-12 | 2002-12-10 | カイロテック・テクノロジー・リミテッド | プロスタグランジンプレカーサーの調製のための方法 |
| WO2006076565A3 (fr) * | 2005-01-14 | 2006-12-07 | Schering Corp | Preparation d'alcool propargylique chiral et d'intermediaires d'ester d'analogues d'himbacine |
| US7897795B2 (en) | 2008-04-09 | 2011-03-01 | Scinopharm Taiwan Ltd. | Process for the preparation of prostaglandin analogues and intermediates thereof |
| US8436194B2 (en) | 2008-04-09 | 2013-05-07 | Scinopharm Taiwan, Ltd. | Process for the preparation of prostaglandin analogues and intermediates thereof |
| US8742143B2 (en) | 2008-04-09 | 2014-06-03 | Scinopharm Taiwan, Ltd. | Process for the preparation of prostaglandin analogues |
| CN103917665A (zh) * | 2011-11-09 | 2014-07-09 | 纳幕尔杜邦公司 | 用于沙门氏菌检测的序列和它们的用法 |
| CN103917665B (zh) * | 2011-11-09 | 2016-11-16 | 纳幕尔杜邦公司 | 用于沙门氏菌检测的序列和它们的用法 |
| WO2020255164A1 (fr) * | 2019-06-21 | 2020-12-24 | Council Of Scientific And Industrial Research | Procédé chimio-enzymatique pour la préparation d'alcool homopropargylique |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2575295A (en) | 1996-01-04 |
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