Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 26, Pages 4927-4930Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200907
Keywords
Carbohydrates; Diastereoselectivity; Glycosylation; Synthetic methods
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Funding
- Tufts University
- GAANN from the U.S. Department of Education
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A mixture of 3,3-dibromocyclopropene and TBAI promotes highly a-selective glycosylation reactions (up to >20:1) by using deoxy sugar hemiacetal donors. The reaction provides a convenient method for generating highly reactive glycosyl donors in situ from shelf-stable starting materials. Both armed and disarmed sugars undergo the reaction, and selectivity is independent of the configuration of the donor sugar.
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