Issue 19, 2010

Facile glycosylation strategy with two-stage activation of allyl glycosyl donors. Application to concise synthesis of Shigella flexneri serotype Y O-antigen

Abstract

A practical, useful glycosylation method employing only allyl glycoside building blocks has been developed. The donor's glycosylation reactivity is turned on via isomerization of its anomeric allyl protecting group into the corresponding prop-1-enyl moiety. Subsequent chemoselective activation with NIS/TfOH achieves high yields in glycosidic bond construction at room temperature. The efficacy and efficiency of this approach in carbohydrate synthesis is demonstrated in the concise synthesis of the fully protected Shigella flexneri serotype Y O-antigen.

Graphical abstract: Facile glycosylation strategy with two-stage activation of allyl glycosyl donors. Application to concise synthesis of Shigella flexneri serotype Y O-antigen

Supplementary files

Article information

Article type
Paper
Submitted
12 Feb 2010
Accepted
21 Jun 2010
First published
03 Aug 2010

Org. Biomol. Chem., 2010,8, 4322-4328

Facile glycosylation strategy with two-stage activation of allyl glycosyl donors. Application to concise synthesis of Shigella flexneri serotype Y O-antigen

Y. Wang, X. Zhang and P. Wang, Org. Biomol. Chem., 2010, 8, 4322 DOI: 10.1039/C002865G

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