Synthesis and stereoselective glycosylation of D- and L-glycero-beta-D-manno-heptopyranoses

Org Lett. 2005 Mar 31;7(7):1395-8. doi: 10.1021/ol050224s.

Abstract

[reaction: see text] A method for the direct stereocontrolled synthesis of D- and L-glycero-beta-D-manno-heptopyranosides such as those found in the repeating unit of the O-specific polysaccharide from the CNCTC 113/92 LPS (serotype 54) is described. The method relies on the presence of a 4,6-O-benzylidene acetal to effect stereocontrol at the anomeric center; the configuration at C6 (L- or D-glycero) is of minimal importance.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbohydrate Sequence
  • Glycosylation
  • Heptoses / chemical synthesis*
  • Lipopolysaccharides / chemistry*
  • Molecular Sequence Data
  • Molecular Structure
  • Plesiomonas / chemistry*
  • Stereoisomerism

Substances

  • Heptoses
  • Lipopolysaccharides