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Studies on Selectin Binding Inhibitors: Synthesis of Sialyl-Lewis X and Sialyl-Lewis A Epitope Analogs Containing 2-Acetamido Derivative ofN-Methyl-1-Deoxynojirimycin1

 

作者: Makoto Kiso,   Hiroyasu Furui,   Hideharu Ishida,   Akira Hasegawa,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1996)
卷期: Volume 15, issue 1  

页码: 1-14

 

ISSN:0732-8303

 

年代: 1996

 

DOI:10.1080/07328309608005420

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

Synthesis of sialyl-Lewis x (15) and sialyl-Lewis a (17) epitope analogs containing the 2-acetamido derivative ofN-methyl-1-deoxynojirimycin has been achieved. A suitably protected 2-acetamido- 1-deoxynojirimycin derivative5, prepared from 1-deoxynojirimycinviathe epoxide intermediate3, was successively coupled with methyl- 1-thioglycosides of L-fucose (6) and β-sialyl-(2→3)-D-galactose (9). The resulting tetrasaccharides (10and13) were each converted, by reductiveN-methylation and deprotection, into the desired epitope analogs.

 

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