Reagent switchable stereoselective beta(1,2) mannoside mannosylation: OH-2 of mannose is a privileged acceptor

Org Biomol Chem. 2008 Aug 7;6(15):2692-6. doi: 10.1039/b803999m. Epub 2008 Jun 2.

Abstract

The discovery of novel conditions for highly beta-stereoselective (>9 : 1) mannosylation of OH-2 of mannosides using a straightforward perbenzylthioglycoside donor has allowed ready assembly of beta-mannosyl oligosaccharides including the repeating trisaccharide motif of the O5 antigen of pathogen Klebsiella pneumoniae.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Hydroxides / chemistry*
  • Mannosides / chemistry*
  • Molecular Structure
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Stereoisomerism
  • Thioglycosides / chemistry

Substances

  • Hydroxides
  • Mannosides
  • Oligosaccharides
  • Thioglycosides
  • hydroxide ion