Synthesis of methyl 3-O-(alpha-D-glucopyranosyl)-7-O-(L-glycero-alpha-D- manno-heptopyranosyl)-L-glycero-alpha-D-manno-heptopyranoside

Carbohydr Res. 1990 Sep 19:205:125-32. doi: 10.1016/0008-6215(90)80133-n.

Abstract

The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranoside and methyl 7-O-L-glycero-alpha-D-manno-heptopyranosyl-L-glycero-alpha-D-manno- heptopyranoside have been synthesised. Methyl 2,3,4-tri-O-benzyl-L-glycero-alpha-D-manno- heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-alpha-D-manno- hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Lipopolysaccharides / chemistry
  • Magnetic Resonance Spectroscopy
  • Methylglycosides / chemical synthesis*
  • Methylglycosides / chemistry
  • Molecular Sequence Data
  • Molecular Structure
  • Salmonella / analysis
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry

Substances

  • Lipopolysaccharides
  • Methylglycosides
  • Trisaccharides
  • methyl 3-O-glucopyranosyl-7-O-heptopyranosyl-heptopyranoside