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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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Publication details

The article was received on 14 Aug 2019, accepted on 30 Sep 2019 and first published on 01 Oct 2019


Article type: Edge Article
DOI: 10.1039/C9SC04079J
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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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

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

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