Document Detail


Thioglycosylation of 1,2-cis-glycosyl acetates: a long-standing overlooked issue in preparative carbohydrate chemistry.
MedLine Citation:
PMID:  21524413     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
1,2-cis-Glycosyl acetates with the α-configuration were revealed to be very unreactive towards Lewis acid catalyzed thioglycosylations. Optimal and cost-effective conditions for enabling this direct conversion is absent in the literature. Our studies have shown that elevating the reaction temperature with a catalytic amount of BF(3)·OEt(2) was more effective than changing Lewis acids with higher acidities to accommodate the low reactivity of α-glycosyl acetates. The effect of impurities in stored BF(3)·OEt(2) on the reaction is also discussed.
Authors:
Ci Xu; Han Liu; Xuechen Li
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-4-6
Journal Detail:
Title:  Carbohydrate research     Volume:  -     ISSN:  1873-426X     ISO Abbreviation:  -     Publication Date:  2011 Apr 
Date Detail:
Created Date:  2011-4-28     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 Elsevier Ltd. All rights reserved.
Affiliation:
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
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