The synthesis and characterization of electron-poor glycosylamines and derived glycosylamides
Jakub Zýka1, Vít Prouza1, Nina Habanová2
1Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague, Technická 5, 166 28, Prague, Czech Republic; Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo Nám. 2, 166 10, Prague, Czech Republic.
Abstract:
This paper describes a unified approach toward diglycosylamines using methanolic ammonia. All the glycosylamines prepared have been fully characterized, and their anomeric configuration has been determined. The article presents a novel method for the N-acylation of diglycosylamines and other electron-poor glycosylamines, which employs nitromethane as a solvent in carboxylic anhydride acylation under acidic conditions. The feasibility of this transformation is represented by a wide range of reaction substrates. All glycosylamides are formed solely with β-configuration. These two reactions constitute a simple and effective route to the synthesis of a novel class of compounds with an N-glycosidic linkage.
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