The Chemical Modification of the C-1 Substituent of A 4-O-Phosphono-O-Glucosamine Derivative (GLA-27) Related to Bacterial Lipid A

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Abstract
1-Thio and 1-O-phosphono derivatives (9-11 and 15) of 2-deoxy–4-O-phosphono-3-O-tetradecanoyl-2-[(3RS)-3-tetradecanoyloxytetradecan-amido]-D-glucose (GLA-27-RS), which exhibits some of the beneficial biological activities of bacterial endotoxin, have been synthesized from benzyl 2-deoxy-4,6-O-isopropylidene-3-O-tetradecanoyl-2-[(3RS)-3-tetradecanoyloxytetradecanamido]-β-O-glucopyranoside (1), and 2-deoxy-4-O-diphenylphosphono-3-O-tetradecanoyl-2-[(3RS)-3-tetra-decanoyloxytetradecanamido]-D-glucopyranose (12), respectively.