Oligosaccharides from "standardized intermediates". Synthesis of a branched tetrasaccharide glycoside isomeric with the blood-group B, type 2 determinant

Carbohydr Res. 1983 Mar 16;114(1):43-52. doi: 10.1016/0008-6215(83)88171-3.

Abstract

Building block derivatives of the component monosaccharides were used to construct the tetrasaccharide glycoside 15, in which an alpha-D-Galp-(1 leads to 4)-D-Gal linkage replaces the alpha-(1 leads to 3) linkage of the human blood-group B, type 2, determinant structure. The initial coupling of 2-O-benzoyl-3,6-di-O-benzyl-4-O-(tetrahydropyran-2-yl)-alpha-D-galactopyranosyl chloride to allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside was followed by selective deprotection of the disaccharide product, either at O-4' (to give 8) or O-2' (to give 3). The conversion of 8 into 15 involved successive coupling with tetra-O-benzyl-alpha-D-galactopyranosyl bromide (8 leads to 11), O-debenzoylation at O-2' (11 leads to 12), coupling with tri-O-benzyl-alpha-L-fucopyranosyl bromide (12 leads to 14), and O-debenzylation by hydrogenolysis (14 leads to 15). Alternatively, 3 was alpha-L-fucosylated to give 6, and 6 was selectively deprotected at O-4' to give 7. However, attempts to alpha-D-galactosylate 7 were unsuccessful. The unsubstituted forms of the intermediate disaccharide (8) and trisaccharide (12) glycosides were obtained by appropriate deblocking procedures.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • ABO Blood-Group System / immunology*
  • Epitopes*
  • Humans
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / immunology
  • Optical Rotation

Substances

  • ABO Blood-Group System
  • Epitopes
  • Indicators and Reagents
  • Oligosaccharides