α-Selective organocatalytic synthesis of 2-deoxygalactosides

Angew Chem Int Ed Engl. 2012 Sep 3;51(36):9152-5. doi: 10.1002/anie.201204505. Epub 2012 Aug 9.

Abstract

Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2-deoxymonosaccharide moiety. The reaction is highly stereoselective for α-linkages and proceeds by way of a syn-addition mechanism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry
  • Catalysis
  • Galactosides / chemical synthesis
  • Galactosides / chemistry*
  • Glycosylation
  • Stereoisomerism
  • Thiourea / chemistry*

Substances

  • Acetals
  • Galactosides
  • Thiourea