Synthesis of new 1,2,3-triazol-carbohydrates

The reaction of a mixture of 1-azide-glycopyranoside (<strong>1</strong>) and appropriate alkynes (<strong>2a-e</strong>), in the presence of CuI/Et<sub>3</sub>N as catalyst system, and acetonitrile as solvent, provided the glycoside triazoles (<strong>3a-e&...

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Bibliographic Details
Main Authors: Bruna M. Guimarães, Ronaldo N. Oliveira
Format: Article
Language:English
Published: Universidade Federal de Mato Grosso do Sul 2012-06-01
Series:Orbital: The Electronic Journal of Chemistry
Subjects:
Online Access:http://orbital.ufms.br/index.php/Chemistry/article/view/343
Description
Summary:The reaction of a mixture of 1-azide-glycopyranoside (<strong>1</strong>) and appropriate alkynes (<strong>2a-e</strong>), in the presence of CuI/Et<sub>3</sub>N as catalyst system, and acetonitrile as solvent, provided the glycoside triazoles (<strong>3a-e</strong>) in moderate-to-excellent yields (<em>60-93%)</em>. We observed that the reactivity of the alcohols decreased due to steric hindrance (prim&gt;sec&gt;terc). Furthermore, the use of ultrasound irradiation was favorable to furnish the desired products with excellent yields and a shorter reaction time, except for the compound (<strong>3e</strong>).       <br />
ISSN:1984-6428