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Issue 45, 2019
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Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens

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Abstract

Studies of S-linked glycoconjugates have attracted growing interest because of their enhanced chemical stability and enzymatic resistance over O-glycoside counterparts. We here report a facile approach to access α-1,2-cis-S-linked glycosides using triflic acid as a catalyst to promote the glycosylation of a series of thiols with D-glucosamine, galactosamine, glucose, and galactose electrophiles. This method is broadly applicable for the stereoselective synthesis of S-linked glycopeptides, oligosaccharides and glycolipids in high yield and excellent α-selectivity. Many of the synthetic limitations associated with the preparation of these S-linked products are overcome by this catalytic method.

Graphical abstract: Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens

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Article information


Submitted
14 Aug 2019
Accepted
30 Sep 2019
First published
01 Oct 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 10475-10480
Article type
Edge Article

Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens

S. Zhu, G. Samala, E. T. Sletten, J. L. Stockdill and H. M. Nguyen, Chem. Sci., 2019, 10, 10475
DOI: 10.1039/C9SC04079J

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