LIPASE-CATALYZED DIACYLATION OF 1,3-BUTANEDIOL

被引:10
作者
EGUCHI, T
MOCHIDA, K
机构
[1] Tokyo Research Laboratories, Kyowa Hakko Kogyo Co. Ltd., Tokyo, 194, Machida
关键词
D O I
10.1007/BF00131763
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
A kinetic resolution of 1,3-butanediol was accomplished by lipase-catalyzed enantioselective diacylations in organic solvent. Diacylation of 1,3-butanediol was carried out using immobilized lipase SP382 (from Candida sp.) to produce (R) -1,3-diacetoxybutane with 85.8% e.e.. And then, this optically active product was chemically hydrolyzed to diol, and re-acylated with lipase SP382 to (R) -1,3-diacetoxybutane with over 98% e.e..
引用
收藏
页码:955 / 960
页数:6
相关论文
共 19 条
[1]   AN ASYMMETRIC-SYNTHESIS OF ALPHA-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER - AN APPLICATION TO THE ASYMMETRIC-SYNTHESIS OF EXO-(+)-BREVICOMIN [J].
ASAMI, M ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1983, (01) :93-96
[2]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[3]  
EGUCHI T, 1993, UNPUB
[4]  
Ferrelra J.T.B., 1990, TETRAHEDRON, V46, P6311
[5]   SYNTHESIS OF (RECIFEIOLIDE) (R)-TRANS-11-HYDROXY-8-DODECENOIC ACID LACTONE [J].
GERLACH, H ;
OERTLE, K ;
THALMANN, A .
HELVETICA CHIMICA ACTA, 1976, 59 (03) :755-760
[6]   ENZYMATIC PREPARATION OF ENANTIOMERICALLY PURE AND SELECTIVELY PROTECTED 1,2-DIOLS AND 1,3-DIOLS [J].
GOERGENS, U ;
SCHNEIDER, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) :1066-1068
[7]   RESOLUTION OF 1,3-ALKANEDIOLS VIA CHIRAL SPIROKETALS DERIVED FROM L-MENTHONE [J].
HARADA, T ;
KUROKAWA, H ;
OKU, A .
TETRAHEDRON LETTERS, 1987, 28 (41) :4843-4846
[8]   ACCESS TO (S)-2-METHYLOXETANE AND THE PRECURSOR (S)-1,3-BUTANEDIOL OF HIGH ENANTIOMERIC PURITY [J].
HINTZER, K ;
KOPPENHOEFER, B ;
SCHURIG, V .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3850-3854
[9]   SYNTHESIS OF OPTICALLY-ACTIVE 25-METHYL-1.6-DIOXA-SPIRO[4.5]DECANE AND 7S-METHYL-1.6-DIOXA-SPIRO[4.5]DECANE, THE PHEROMONE COMPONENTS OF PARAVESPULA-VULGARIS (L), FROM S-ETHYL LACTATE [J].
HINTZER, K ;
WEBER, R ;
SCHURIG, V .
TETRAHEDRON LETTERS, 1981, 22 (01) :55-58
[10]  
HOFFMANN RW, 1987, LIEBIGS ANN CHEM, P977