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

Article abstract of DOI:10.1016/S0040-4020(97)10063-1

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.