Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B
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 enantiome...
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ftczechacademysc:oai:kramerius.lib.cas.cz:uuid:5ea68e56-be79-11e2-9ddd-001e65b2b442 2024-03-17T08:53:39+00:00 Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B Orrenius Christian Sandell Johan Unelius C. Rikard 525 533 electronic https://kramerius.lib.cas.cz/view/uuid:5ea68e56-be79-11e2-9ddd-001e65b2b442 https://doi.org/10.1135/cccc19980525 en eng https://kramerius.lib.cas.cz/view/uuid:5ea68e56-be79-11e2-9ddd-001e65b2b442 doi:http://dx.doi.org/10.1135/cccc19980525 policy:private Candida antarctica lipase B Enzymatic resolution 4-Methylheptan-3-ol model:article ftczechacademysc https://doi.org/10.1135/cccc19980525 2024-02-19T22:41:49Z 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%. Article in Journal/Newspaper Antarc* Antarctica Czech Academy of Sciences: dKNAV Collection of Czechoslovak Chemical Communications 63 4 525 533 |
institution |
Open Polar |
collection |
Czech Academy of Sciences: dKNAV |
op_collection_id |
ftczechacademysc |
language |
English |
topic |
Candida antarctica lipase B Enzymatic resolution 4-Methylheptan-3-ol |
spellingShingle |
Candida antarctica lipase B Enzymatic resolution 4-Methylheptan-3-ol Orrenius Christian Sandell Johan Unelius C. Rikard Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B |
topic_facet |
Candida antarctica lipase B Enzymatic resolution 4-Methylheptan-3-ol |
description |
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%. |
format |
Article in Journal/Newspaper |
author |
Orrenius Christian Sandell Johan Unelius C. Rikard |
author_facet |
Orrenius Christian Sandell Johan Unelius C. Rikard |
author_sort |
Orrenius Christian |
title |
Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B |
title_short |
Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B |
title_full |
Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B |
title_fullStr |
Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B |
title_full_unstemmed |
Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B |
title_sort |
enantioselective preparation of the stereoisomersof 4-methylheptan-3-ol using candida antarctica lipase b |
url |
https://kramerius.lib.cas.cz/view/uuid:5ea68e56-be79-11e2-9ddd-001e65b2b442 https://doi.org/10.1135/cccc19980525 |
op_coverage |
525 533 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
https://kramerius.lib.cas.cz/view/uuid:5ea68e56-be79-11e2-9ddd-001e65b2b442 doi:http://dx.doi.org/10.1135/cccc19980525 |
op_rights |
policy:private |
op_doi |
https://doi.org/10.1135/cccc19980525 |
container_title |
Collection of Czechoslovak Chemical Communications |
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63 |
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4 |
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525 |
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533 |
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1793767063039246336 |