Synthesis of 2-Deoxy-2-[(2S, 3R)-(2-fluoro-3-hydroxytetradecanoyl)amino]-3-O-[(3R)-3-tetradecanoyloxytetradecanoyl]-D-glucopyranose 4-(Dihydrogen Phosphate) and 2-Deoxy-2-[(2R, 3S)-(2-fluoro-3-hydroxytetradecanoyl)amino]-3-O-[(3R)-3-tetradecanoyloxytetradecanoyl]-D-glucopyranose 4-(Dihydrogen Phosphate)

Abstract

2-Deoxy-2-[(2S, 3R)-(2-fluoro-3-hydroxytetradecanoyl)amino]3-O-[(3R)-3-tetradecanoyloxytetradecanoyl]-D-glucopyranose 4-(dihydrogen phosphate) and 2-deoxy-2-[(2R, 3S)-(2-fluoro-3-hydroxytetradecanoyl)amino]-3-O-[(3R)-3-tetradecanoyloxytetradecanoyl]-D-glucopyranose 4-(dihydrogen phosphate) were synthesized. The (2S, 3R)-compound (9a) was a little more active than GLA-60 in the prostaglandin D_2 releasing test on macrophages, and the(2R, 3S)-compound (9b) was almost inactive.

Journal

Chemical & pharmaceutical bulletin   [List of Volumes]

Chemical & pharmaceutical bulletin 40(2), 333-337, 1992-02-25  [Table of Contents]

The Pharmaceutical Society of Japan

Cited by:  1

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