Chemistry of bacterial endotoxins. Part 4. Synthesis of anomeric 2-deoxy-2[(3R)-3-hydroxytetradecanamido]-D-glucopyranosyl phosphate and pyrophosphate derivatives related to ‘Lipid A’

Abstract

Syntheses of both anomers of 2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-D-glucopyranosyl phosphate and of 2-amino-2-deoxy-D-glucopyranosyl 2-aminoethyl phosphate are reported, as well as those of two pyrophosphate derivatives of glucosamine, namely 2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-α-D-glucopyranosyl pyrophosphate and P¹-(2-aminoethyl)P²-{2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-α-D-glucopyranosyl}pyrophosphate, structures that have been identified as being present in the hydrophobic region (Lipid A) of endotoxins.