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Enantioselective preparation of the stereoisomers of 4-methylheptan-3-ol using Candida antarctica lipase B
KTH, Sweden.ORCID iD: 0000-0001-7158-6393
KTH, Sweden.
KTH, Sweden.
1998 (English)In: Collection of Czechoslovak Chemical Communications, ISSN 0010-0765, E-ISSN 1212-6950, Vol. 63, no 4, 525-533 p.Article in journal (Refereed) Published
Abstract [en]

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-methylheptan-3-ols was developed. The optical purity of the separated isomers was in the range of 29-97%.

Place, publisher, year, edition, pages
1998. Vol. 63, no 4, 525-533 p.
Keyword [en]
4-methylheptan-3-ol, candida antarctica lipase b, enzymatic resolution, ant leptogenys-diminuta, acyl transfer-reactions, elm bark beetle, catalyzed transesterification, quantitative-analyses, kinetic resolutions, pheromone synthesis, secondary alcohols, ethyl-octanoate, boronic esters
National Category
Natural Sciences
Research subject
Natural Science, Organic Chemistry; Natural Science, Ecological chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-14112ISI: 000073909800006OAI: oai:DiVA.org:lnu-14112DiVA: diva2:440834
Note

Zq855 Times Cited:4 Cited References Count:31

Available from: 2011-09-13 Created: 2011-09-13 Last updated: 2017-01-11Bibliographically approved

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Unelius, C. Rikard
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