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.

Department of Analytical Chemistry 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

Department 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

Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo Nám 2 166 10 Prague Czech Republic

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