SYNTHESIS OF 2-DEOXY-2-[(3R)-3-HYDROXYACYL]AMINO-4-O-PHOSPHONO-3-O-[(3R)-3-TETRADECANOYLOXYTETRADECANOYL]-D-GLUCOPYRANOSE DERIVATIVES RELATED TO BACTERIAL LIPID-A

被引:7
作者
OGAWA, Y
FUJISHIMA, Y
ISHIDA, H
KISO, M
HASEGAWA, A
机构
[1] Department of Applied Bioorganic Chemistry, Gifu University, Gifu
关键词
D O I
10.1080/07328309008543859
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Lipid A subunit analogs, the 4-0-phosphono-o-glucosamine derivatives (14-16: GLA 93–95) which carry 2-N-linked 3-hydroxyacyl groups, were synthesized. 2-(Trimethylsilyl)ethyl 2-amino-2-deoxy-4,6-0-isopropylidene-β-o-glucopyranoside (1) was transformed into 2-(trimethylsilyl)ethyl 2-amino-6-0-tert-butyldimethylsilyl-2-deoxy-4-0-diphenylphosphono-3-G-[(3R)-3-tetradecanoyloxytetradecanoyl]-B- D-glucopyranoside (7) through several steps. N-Acylation of 7 with 3-hydroxyl fatty acids gave the corresponding 8–10, which were converted, via the cleavage of protecting groups, into a series of desired compounds. © 1990, Taylor & Francis Group, LLC. All rights reserved.
引用
收藏
页码:643 / 652
页数:10
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