Stereoselective glycosylation of exo-glycals accelerated by Ferrier-type rearrangement

Org Lett. 2003 Apr 3;5(7):1087-9. doi: 10.1021/ol034130z.

Abstract

[reaction: see text] Owing to the driving force of the Ferrier-type rearrangement, the exo-glycals are highly reactive with various alcohols to afford glycosides and glycoconjugates with exclusive alpha-configuration. The resulting vinyl group in these glycosylation products can be further elaborated for general applications, including the synthesis of spiro derivatives and glycosylation of 2-ketoaldonic acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycoconjugates / chemical synthesis*
  • Glycoconjugates / chemistry
  • Glycosides / chemical synthesis
  • Glycosides / chemistry*
  • Glycosylation
  • Molecular Structure

Substances

  • Glycoconjugates
  • Glycosides