Chemistry of bacterial endotoxins. Part 1. Block synthesis of 6-O-{4-O-ammonio(hydrogen)phosphono-2-deoxy-2-[(3R)-3-hydroxy-tetradecanamido]-β-D-glucopyranosyl}-2-deoxy-2-[(3R)-3-hydroxy-tetradecanamido]-D-glucose

Abstract

The synthesis of the disaccharide present in the hydrophobia region of many endotoxins, a 2-amino-2-deoxy-β-D-glucopyranosyl-(1 → 6)-2-amino-2-deoxy-D-glucose in which the amino groups are acylated by (3R)-3-hydroxytetradecanoic acid residues and the 4″-hydroxy group is esterified by phosphate, is described. Two synthons carrying the specific substituents were prepared and condensed; stepwise removal of the protecting groups from the disaccharide thus formed afforded the title compound.