Practical synthesis of the disaccharide epitope, D-galactopyranosyl-alpha-1,3-D-galactopyranose, by using 1,2;5,6-di-O-cyclohexylidene-alpha-D-galactofuranose as the glycosyl acceptor

Biosci Biotechnol Biochem. 2000 Sep;64(9):1974-7. doi: 10.1271/bbb.64.1974.

Abstract

D-Galactosyl-alpha-1,3-D-galactopyranose (1) was chemically prepared in a good yield by coupling phenyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside (5) or 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl bromide (8) with 1,2:5,6-di-O-cyclohexylidene-alpha-D-galactofuranose (3) with subsequent de-O-benzylation and de-O-cyclohexylidenation of the resulting protected alpha1,3-disaccharide.

MeSH terms

  • Carbohydrate Conformation
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Epitopes / chemistry*
  • Galactose / analogs & derivatives*
  • Indicators and Reagents
  • Models, Molecular

Substances

  • 1,2-5,6-di-O-cyclohexylidene-galactofuranose
  • Disaccharides
  • Epitopes
  • Indicators and Reagents
  • galactosyl-(1-3)galactose
  • Galactose