198770-48-8

Upstream product

• 87357-67-3 (R)-3-benzyloxytetradecanoic acid 
• 179530-53-1 2,6-anhydro-3-azido-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile 
• 99701-76-5 Acetic acid (2R,3S,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-cyano-tetrahydro-pyran-4-yl ester 
• 145840-43-3 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate 
• 94715-56-7 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 
• 94715-57-8 O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl) trichloroacetimidate 

Downstream Products

• 179530-65-5 (2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester 
• 179530-61-1 (4aR,6S,7R,8R,8aS)-7-((R)-3-Benzyloxy-tetradecanoylamino)-2,2-dimethyl-8-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid benzhydryl ester 
• 179530-62-2 (2S,3R,4R,5S,6R)-3-((R)-3-Benzyloxy-tetradecanoylamino)-5-hydroxy-6-hydroxymethyl-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester 
• 214050-96-1 diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptonate 
• 214050-97-2 diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate 
• 179530-59-7 diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptonate 
• 179530-57-5 diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-D-glycero-D-ido-heptonate 

Relevant academic research and scientific papers

Lipid A-type pyrancarboxylic acid derivatives, their synthesis and their biological activities

Synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing sugar part of the disaccharide instead of the phosphoric acid group in lipid A, is described. We investigated the influence of the substituents in the 2'- and 6'-position of the molecules synthesized on their activities toward human monoblastic U937 cells. It was revealed that a series of compounds, possessing an acetamido group in the 2'-position showed strong LPS-antagonistic activity. (C) 2000 Elsevier Science Ltd.

Syntheses of 2,6-anhydro-3-deoxy-5-O-phosphono-3-tetradecanamido-4-O- [(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-heptonic acid, its dimeric analogue, and related compounds

Pyran carboxylic acid analogues of GLA-60 (12a, 12b, and 17) and their dimeric analogues (21 and 24) were synthesized in a stereocontrolled manner. Compounds 12a and 17 showed endotoxin antagonistic activity toward human monoblastic U937 cells as an index of the inhibition of LPS-induced TNFα production. Compounds 12b and 24 were less active than 12a and 17, Dimeric ester 21 was practically inactive.