Synthesis of a hexasaccharide that relates to the arabinogalactan epitope

Carbohydr Res. 2001 Nov 8;336(2):99-106. doi: 10.1016/s0008-6215(01)00259-2.

Abstract

A hexasaccharide derivative of the arabinogalactan epitope, methyl beta-D-galactopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->3)]-beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->3)]-alpha-D-galactopyranoside, was synthesized efficiently using a 3+3 strategy. The key step is the preparation of the trisaccharide donor, isopropyl 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1-->6)-[2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl-(1-->3)]-2,4-di-O-benzoyl-1-thio-beta-D-galactopyranoside, from isopropyl 1-thio-beta-D-galactopyranoside using a one-pot synthesis of a 3,6-differentially protected building block.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epitopes / chemistry*
  • Galactans / chemistry*
  • Isopropyl Thiogalactoside / chemistry*
  • Oligosaccharides, Branched-Chain / chemical synthesis*
  • Trisaccharides / chemical synthesis*

Substances

  • Epitopes
  • Galactans
  • Oligosaccharides, Branched-Chain
  • Trisaccharides
  • Isopropyl Thiogalactoside
  • arabinogalactan