179530-63-3

Upstream product

• 198770-39-7 Tetradecanoic acid ((4aR,6S,7R,8R,8aS)-6-cyano-8-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-amide 
• 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 
• 87357-76-4 (R)-3-(dodecanoyloxy)tetradecanoic acid 
• 179530-58-6 (4aR,6S,7R,8R,8aS)-8-Hydroxy-2,2-dimethyl-7-tetradecanoylamino-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid benzhydryl ester 
• 179530-54-2 Tetradecanoic acid (4aR,6S,7S,8R,8aS)-6-cyano-2,2-dimethyl-7-tetradecanoylamino-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 179530-56-4 (2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-tetradecanoylamino-tetrahydro-pyran-2-carboxylic acid benzhydryl ester 
• 179530-53-1 2,6-anhydro-3-azido-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile 
• 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 
• 179530-60-0 (4aR,6S,7R,8R,8aS)-2,2-Dimethyl-7-tetradecanoylamino-8-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid benzhydryl ester 

Downstream Products

• 183479-80-3 diphenylmethyl 2,6-anhydro-7-O-{2,6-anhydro-7-O-benzyloxycarbonyl-3-deoxy-5-O-diphenylphosphono-3-tetradecanamido-4-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-heptonyl}-3-deoxy-3-tetradecanamino-4-O-[(R)-3-(tetradecanoyloxy)tetradecano... 
• 183479-78-9 (2S,3R,4R,5S,6R)-5-(Diphenoxy-phosphoryloxy)-6-hydroxymethyl-3-tetradecanoylamino-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid 
• 183479-79-0 (2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-5-(diphenoxy-phosphoryloxy)-3-tetradecanoylamino-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid 
• 179530-66-6 (2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-5-(diphenoxy-phosphoryloxy)-3-tetradecanoylamino-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester 
• 179530-67-7 (2S,3R,4R,5S,6R)-5-(Diphenoxy-phosphoryloxy)-6-hydroxymethyl-3-tetradecanoylamino-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester 
• 198770-40-0 (2S,3R,4R,5S,6S)-5-(Diphenoxy-phosphoryloxy)-6-fluoromethyl-3-tetradecanoylamino-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester 
• 179530-64-4 (2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-5-hydroxy-3-tetradecanoylamino-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester 

Relevant academic research and scientific papers

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.

Synthesis of 2,6-anhydro-3-deoxy-5-O-phosphono-3-tetradecanamido-4-O-[(R)-3-(tetrad ecanoyloxy)tetradecanoyl]-D-glycero-D-ido-heptonic acid as a new potent endotoxin antagonist and its dimeric analogue

A pyran carboxylic acid analogue of GLA-60 (14) and its dimeric analogue 18 were synthesized in a stereocontrolled manner. Compound 14 showed strong LPS-antagonistic activity.