Synthesis of some biologically relevant beta-C-glycoconjugates

Org Lett. 2003 May 15;5(10):1721-3. doi: 10.1021/ol034363q.

Abstract

[reaction: see text] An esterification-RCM approach to a variety of biologically relevant beta-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then converted to the final ring-closed product 6 in three steps in 49-60% overall yield. The formed compounds are biologically relevant and serve as stable carbohydrate mimics of the corresponding O-glycosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Esters / chemical synthesis
  • Glycoconjugates / chemical synthesis*
  • Glycosides / chemical synthesis
  • Glycosylation
  • Indicators and Reagents

Substances

  • Esters
  • Glycoconjugates
  • Glycosides
  • Indicators and Reagents