Synthesis of 2-deoxy-2-[(2,2-difluoro-3-hydroxytetradecanoyl)amino]-3-O- [(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glucopyranose 4-phosphate.
2-Deoxy-2-[(2,2-difluoro-3-hydroxytetradecanoyl)amino]-3-O-[(R)-3- (tetradecanoyloxy)tetradecanoyl]-D-glucopyranose 4-phosphates (9H,L) were synthesized from allyl 2-amino-2-deoxy-4,6-O- isopropylidene-beta-D-glucopyranoside (1), (+/-)-3-[(benzyloxycarbonyl)oxy]-2,2-difluorotetradecanoic acid, and (R)-3- (tetradecanoyloxy)tetradecanoic acid. Both compounds 9H and 9L were more active than GLA-60 for the prostaglandin D2 releasing test on macrophages.
Shiozaki
M
M
New Lead Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Kobayashi
Y
Y
Arai
M
M
Watanabe
T
T
Hiraoka
T
T
D000818:Animals; D002460:Cell Line; D055598:Chemical Phenomena; D002621:Chemistry; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D010529:Peritoneal Cavity / Q000166:cytology; D015230:Prostaglandin D2 / Q000378:metabolism
D008050:Lipid A; C056260:GLA 60; C070501:2-deoxy-2-((2,2-difluoro-3-hydroxytetradecanoyl)amino)-3-O-(3-(tetradecanoyloxy)tetradecanoyl)glucopyranose 4-phosphate; D015230:Prostaglandin D2