Synthesis of Sialyl Lewis X Ganglioside Analogs Containing A Variable Length Spacer Between the Sugar and Lipophilic Moieties1
作者:
Keisuke Adachi,
Yutaka Yamada,
Hiroaki Wada,
Akihiko Kameyama,
Hideharu Ishida,
Makoto Kiso,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 4-5
页码: 595-607
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808002340
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Five sialyl Lew is X ganglioside analogs containing 4-(2-tetradecylhexadecanoylamino)benzyl group in place of ceramide and a variety of lengths of ethylene glycol chains as the spacer, have been synthesized. Glycosidation ofO-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-glacto-2-nonulopyranosylonate)-(2→3)-O-(4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1→4)-O-[(2,3,4-tri-O-acetylα-L-fucopyranosyl)-(1→3)]-2,4-di-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (13) with oligo ethyleneglycol monobenzyl ether derivatives9, 10, 11and12, prepared from the corresponding oligo ethyleneglycols by 4-nitrobenzylation, reduction andN-acylation with 2-tetradecylhexadecanoic acid, using boron trifluoride etherate gave the corresponding glycolipid derivatives14, 15, 16and17. A similar glycosidation of13with 4-nitrobenzyl alcohol gave the 4-nitrobenzyl glycoside18, which was convertedviareduction of nitro group andN-acylation into the corresponding glycolipid derivative19. Compounds14-17and19were transformed into the title compounds byO-deacylation and hydrolysis of methyl ester group in good yields.
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