Stereodirected synthesis of aryl alpha-C-glycosides from 2-O-arylsilyl-glucopyranosides

Org Lett. 2003 Oct 2;5(20):3763-6. doi: 10.1021/ol035529q.

Abstract

[reaction: see text] An efficient procedure for the stereoselective synthesis of aryl alpha-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.

MeSH terms

  • Benzyl Compounds / chemical synthesis*
  • Benzyl Compounds / chemistry
  • Carbohydrate Conformation
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Organosilicon Compounds / chemistry*
  • Pyrans / chemistry
  • Stereoisomerism

Substances

  • Benzyl Compounds
  • Glycosides
  • Organosilicon Compounds
  • Pyrans