Versatile synthesis and mechanism of activation of S-benzoxazolyl glycosides

J Org Chem. 2007 Aug 31;72(18):6938-46. doi: 10.1021/jo0711844. Epub 2007 Aug 4.

Abstract

As a part of a program for developing new efficient procedures for stereoselective glycosylation, a range of S-benzoxazolyl (SBox) glycosides have been synthesized. The mechanistic aspects of the SBox moiety activation for glycosylation via a variety of conceptually different pathways in the presence of thiophilic, electrophilic, or metal-based promoters have been investigated.

Publication types

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

MeSH terms

  • Alkylation
  • Benzoxazoles / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Glycosides / chemical synthesis
  • Glycosides / chemistry*
  • Ions / chemistry
  • Metals / chemistry
  • Models, Molecular
  • Molecular Structure
  • Protons

Substances

  • Benzoxazoles
  • Glycosides
  • Ions
  • Metals
  • Protons