Syntheses of 2-Deoxy-2-[(2R, 3S)-2-fluoro-3-hydroxytetradecanamido]-3-O-[(3R)-3-hy-droxytetradecanoyl]-4-O-phosphono-D-glucopyranose and Its (2S, 3R)-Isomer

抄録

2-Deoxy-2- [(2R, 3S) -2-fluoro- 3-hydroxytetradecanamido ]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-D-glucopyranose and its (2S, 3R)-isomer were respectively synthesized from allyl 2-[(2R, 3S)-3-(benzyloxycarbonyloxy)-2-fluorotetradecanamido]-2-deoxy-4, 6-O-isopropylidene-β-D-glucopyranoside and its corresponding (2S, 3R)-isomer. Both target compounds did not activate macrophage, but the (2S, 3R)-analogue strongly inhibited the binding of LPS to macrophage.