The synthesis and characterization of electron-poor glycosylamines and derived glycosylamides

0583289 - ÚOCHB 2025 RIV NL eng J - Journal Article
Zýka, Jakub - Prouza, Vít - Habanová, Nina - Pohl, Radek - Parkan, Kamil
The synthesis and characterization of electron-poor glycosylamines and derived glycosylamides.
Carbohydrate Research. Roč. 536, February (2024), č. článku 109023. ISSN 0008-6215. E-ISSN 1873-426X
R&D Projects: GA ČR(CZ) GA22-17586S
Institutional support: RVO:61388963
Keywords : glycosylamides * N-acylation * N-glycosylation * glycosylamines
Impact factor: 3.1, year: 2022
Method of publishing: Limited access
https://doi.org/10.1016/j.carres.2024.109023

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.
Permanent Link: https://hdl.handle.net/11104/0351291