Stereochemistry in the synthesis and reaction of exo-glycals

J Org Chem. 2002 May 31;67(11):3773-82. doi: 10.1021/jo0255227.

Abstract

Two general methods are explored for the stereoselective synthesis of exo-glycals. One method utilizes a nucleophilic addition of fully protected sugar lactones of gluco-, galacto-, and manno-types, followed by the subsequent dehydration, to give the desired exo-glycals with (Z)-configuration. The other method proceeds with selenylation of C-glycosides in a stereoselective manner. The subsequent selenoxide elimination also provides (Z)-exo-glycals. The prepared exo-glycal conjugated esters of either gluco- or manno-type react with allyl alcohol to give exclusively alpha-anomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrates / chemical synthesis*
  • Galactose / chemistry
  • Lactones / chemistry
  • Mannose / chemistry
  • Stereoisomerism

Substances

  • Carbohydrates
  • Lactones
  • Mannose
  • Galactose