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Kahne Glycosylation

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr354

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Kahne Glycosylation. Comprehensive Organic Name Reactions and Reagents. 354:1593–1596.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Kahne glycosylation is a convenient synthesis of glycosides and disaccharides or oligosaccharides between glycosyl phenyl sulfoxide and an acceptor in the presence of a glycosylation promoter. This reaction is particularly useful for unreactive acceptors, or the most hindered alcohols. The promoters for this reaction are triflic anhydride (Tf2O) and trimethylsilyl triflate (TMSOTf) in a stoichiometric amount or triflic acid in a catalytic amount. This reaction has been further extended to glycosyl alkyl sulfoxide and glycosyl disulfide. This reaction has been widely applied for the synthesis of glycosides, disaccharides, and oligosaccharides.

Keywords:

  • oligosaccharides;
  • β-glycosides;
  • trimethylsilyl triflate (TMSOTf);
  • triflic anhydride (Tf2O)