STUDIES ON LACTAMS .96. STEREOSPECIFIC GLYCOSYLATION VIA FERRIER REARRANGEMENT FOR OPTICAL RESOLUTION

Diastereospecific glycosylation of racemic alcohols by reaction with suitable glycal derivatives in the presence of iodine provides easy access to both enantiomers as illustrated by the preparation of an optically pure alpha-hydroxy beta-lactam that is an intermediate for the semisynthesis of taxol.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 59; no. 17; pp. 4714 - 4716
Main Authors BANIK, BK, MANHAS, MS, BOSE, AK
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 26.08.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OLIGOSACCHARIDES
ENANTIOSPECIFIC SYNTHESIS
ANALOGS
TAXOL
STRATEGY
ESTERS
GLYCALS
C-13 SIDE-CHAIN
DERIVATIVES
BETA-LACTAMS
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Summary:Diastereospecific glycosylation of racemic alcohols by reaction with suitable glycal derivatives in the presence of iodine provides easy access to both enantiomers as illustrated by the preparation of an optically pure alpha-hydroxy beta-lactam that is an intermediate for the semisynthesis of taxol.
ISSN:0022-3263
DOI:10.1021/jo00096a004