192196-09-1Relevant articles and documents
New efficient synthesis of a biosynthetic precursor of lipid A
Oikawa, Masato,Wada, Akira,Yoshizaki, Hiroaki,Fukase, Koichi,Kusumoto, Shoichi
, p. 1435 - 1440 (2007/10/03)
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.