Stereoselective entry to beta-linked C-disaccharides using a carbon-Ferrier reaction

Org Lett. 2003 May 15;5(10):1649-52. doi: 10.1021/ol030023t.

Abstract

[structure: see text] The synthesis of unsaturated beta-linked C-disaccharides by the Lewis acid-mediated reaction of 3-O-acetylated glycals with monosaccharide-derived alkenes is described. Deprotection and selective hydrogenation of an exocyclic carbon-carbon double, in the presence of an endocyclic double bond, for representative targets is also illustrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Carbohydrate Sequence
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Indicators and Reagents
  • Molecular Sequence Data
  • Stereoisomerism

Substances

  • Disaccharides
  • Indicators and Reagents