Synthesis of 2-deoxy-4-O-phosphono-3-O-tetradecanoyl-2-[(3R)- and (3S)-3-tetradecanoyloxytetradecanamido]-D-glucose: a diastereoisomeric pair of 4-O-phosphono-D-glucosamine derivatives (GLA-27) related to bacterial lipid A.
The diastereoisomeric, 4-O-phosphono-D-glucosamine derivatives named in the title have been synthesized, starting from benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside and (3RS)-3-hydroxytetradecanoic acid.
M
M
Kiso
S
S
Tanaka
M
M
Tanahashi
Y
Y
Fujishima
Y
Y
Ogawa
A
A
Hasegawa
D007202:Indicators and Reagents; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D013237:Stereoisomerism
D007202:Indicators and Reagents; D008050:Lipid A; C048988:GLA 27