Stereospecific uncatalyzed alpha-O-glycosylation and alpha-C-glycosidation by means of a new D-Gulal-derived alpha vinyl oxirane

J Org Chem. 2004 Oct 15;69(21):7383-6. doi: 10.1021/jo0491152.

Abstract

The reaction of alpha vinyl oxirane 5, prepared through a new route to the d-gulal system, with O-nucleophiles (alcohols and di-O-isopropylidene-alpha-d-monosaccharides) and C-nucleophiles (lithium alkyls) affords, in a completely stereoselective way, the corresponding 2-unsaturated alpha O- and C-glycosides having the same configuration as the starting epoxide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epoxy Compounds / chemical synthesis*
  • Glycosides / chemical synthesis*
  • Glycosylation
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Epoxy Compounds
  • Glycosides
  • 3,4-epoxy-1-butene