Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B

• Published in: Collection of Czechoslovak Chemical Communications
• Main Authors: Orrenius Christian, Sandell Johan, Unelius C. Rikard
• Format: Article in Journal/Newspaper
• Language: English
• Subjects: Candida antarctica lipase B; Enzymatic resolution; 4-Methylheptan-3-ol; Antarc*; Antarctica
• Online Access: https://kramerius.lib.cas.cz/view/uuid:5ea68e56-be79-11e2-9ddd-001e65b2b442; https://doi.org/10.1135/cccc19980525

The four stereoisomers of 4-methylheptan-3-ol were prepared through fractional crystallization of a mixture of their racemic 4-methylhept-3-yl 3,5-dinitrobenzoates, followed by hydrolysis of each crystalline racemate and enantioselective, lipase-mediated transesterification of each pair of enantiomeric alcohols liberated, using the Candida antarctica lipase B as catalyst and S-ethyl octanethioate as the acyl donor. An analytical method of determining the enantiomeric composition of mixtures of 4-methyl-heptan-3-ols was developed. The optical purity of the separated isomers was in the range of 29-97%.