Enantiomerically Pure α,β-Unsaturated Five-Membered-Ring Aldehydes by Ring Contraction of Epoxyhexopyranosides

A series of epoxyhexopyranosides, variously substituted in the 6-position, were each transformed by ring contraction into a single, enantiomerically pure, α,β-unsaturated furanosidic aldehyde. Similar ring contraction of a C-propylglycosidic analog of one of the epoxyhexopyranosides gave a mixture o...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 62; no. 23; pp. 7972 - 7977
Main Authors Pontén, Fritiof, Magnusson, Göran
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.11.1997
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SESQUITERPENES
REARRANGEMENT
EPOXIDES
EFFICIENT SYNTHESIS
2,3-EPOXYCYCLOHEXANOLS
OXIRANES
INTRAMOLECULAR REACTIONS
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Summary:A series of epoxyhexopyranosides, variously substituted in the 6-position, were each transformed by ring contraction into a single, enantiomerically pure, α,β-unsaturated furanosidic aldehyde. Similar ring contraction of a C-propylglycosidic analog of one of the epoxyhexopyranosides gave a mixture of two diastereomeric aldehydes. This finding supports the previously suggested mechanism of the reaction and indicates that O-glycosidic epoxypyranosides also rearrange into two aldehydes, one of which is unstable.
Bibliography:ark:/67375/TPS-5CHXTD3Q-K
Abstract published in Advance ACS Abstracts, October 1, 1997.
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo970666k