Studies on Selectin Binding Inhibitors: Synthesis of Sialyl-Lewis X and Sialyl-Lewis A Epitope Analogs Containing 2-Acetamido Derivative ofN-Methyl-1-Deoxynojirimycin1
- 1 January 1996
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 15 (1) , 1-14
- https://doi.org/10.1080/07328309608005420
Abstract
Synthesis of sialyl-Lewis x (15) and sialyl-Lewis a (17) epitope analogs containing the 2-acetamido derivative of N-methyl-1-deoxynojirimycin has been achieved. A suitably protected 2-acetamido- 1-deoxynojirimycin derivative 5, prepared from 1-deoxynojirimycin via the epoxide intermediate 3, was successively coupled with methyl- 1-thioglycosides of L-fucose (6) and β-sialyl-(2→3)-D-galactose (9). The resulting tetrasaccharides (10 and 13) were each converted, by reductive N-methylation and deprotection, into the desired epitope analogs.Keywords
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