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Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed.by a Bifunctional Organocatalyst
Journal article   Open access  Peer reviewed

Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed.by a Bifunctional Organocatalyst

Sandra Medina, Matthew J. Harper, Edward I. Balmond, Silvia Miranda, Giacomo E. M. Crisenza, Diane M. Coe, Eoghan M. McGarrigle and M. Carmen Galan
Organic letters, Vol.18(17), pp.4222-4225
02/09/2016
DOI: https://doi.org/10.1021/acs.orglett.6b01962
PMID: 27529800

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
The use of a bifunctional cinchona/thiourea organocatalyst for the direct and alpha-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.
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https://doi.org/10.1021/acs.orglett.6b01962View
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