Direct synthesis of diastereomerically pure glycosyl sulfonium salts

Org Lett. 2011 Jun 3;13(11):2928-31. doi: 10.1021/ol2009818. Epub 2011 May 12.

Abstract

It is reported that stable glycosyl sulfonium salts can be generated via direct anomeric S-methylation of ethylthioglycosides. Mechanistically, this pathway represents the first step in the activation of thioglycosides for glycosidation; however, it can further allow for the synthesis and isolation of quasi-stable sulfonium ions, representing a new approach for studying these key intermediates.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Sulfonium Compounds / chemical synthesis*
  • Sulfonium Compounds / chemistry
  • Thioglycosides / chemical synthesis*
  • Thioglycosides / chemistry

Substances

  • Sulfonium Compounds
  • Thioglycosides