99519-06-9

Upstream product

• 87357-67-3 (R)-3-benzyloxytetradecanoic acid 

Downstream Products

• 177085-88-0 N-[(R)-3-(benzyloxy)tetradecanoyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine 
• 179530-55-3 (R)-3-Benzyloxy-tetradecanoic acid (4aR,6S,7S,8R,8aS)-7-((R)-3-benzyloxy-tetradecanoylamino)-6-cyano-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 177085-89-1 N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-β-D-glucopyranosylamine 
• 177085-90-4 N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine 
• 177085-93-7 3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine 
• 177085-92-6 N-[(R)-3-(benzyloxy)tetradecanoyl]-3-O-diphenylphosphono-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine 
• 177085-91-5 N-[(R)-3-(benzyloxy)tetradecanoyl]-3-O-diphenylphosphono-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine 
• 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 
• 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 
• 99519-07-0 allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside 

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.

The first syntheses of GLA-60 positional isomers and their biological activities

Six GLA-60 positional isomers (8, 14, 14', 20, 26, and 26') were synthesized to investigate their biological activities. Compound 8 exhibited potent agonistic activity, while compounds 26 and 26' exhibited slight agonistic activity on TNFα production toward human monoblastic U937 cells. TNFα production (% control; 10 ng ml- of LPS = 100) of compound 8 in the concentration of 10 μM was 611, and that of lipid A in the same concentration was 651. In contrast, the difluorinated compounds 14, 14', and 20 showed little agonistic activity on TNFα production. And neither compound 8 nor compounds 26 and 26' showed antagonistic activity. On the other hand, the difluorinated compounds 14, 14', and 20 showed potent antagonistic activity, and inhibited the LPS-induced TNFα production dose-dependently. Compound 14' (10 μM) inhibited in excess of 80% of the LPS-induced TNFα production.