New efficient synthesis of a biosynthetic precursor of lipid A

Article abstract of DOI:10.1246/bcsj.70.1435

A biosynthetic precursor of lipid A has been synthesized by an improved efficient method. Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)tetradecanoic acid and then coupled by the Lewis acid-promoted glycosidation via the correspending trichloroacetimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yield through 13 steps from N-Troc-D-glucosamine.