Issue 17, 2006
From the journal:

Organic & Biomolecular Chemistry

First synthesis of 1,2,3-triazolo-linked (1,6)-α-d-oligomannoses (triazolomannoses) by iterative Cu(i)-catalyzed alkyne–azide cycloaddition†‡

Pavel Cheshev,a   Alberto Marra*a  and  Alessandro Dondoni*a  

* Corresponding authors

a Laboratorio di Chimica Organica, Dipartimento di Chimica, Via Borsari 46, 44100 Ferrara, Italy
E-mail: adn@unife.it
Fax: 39 0532 291167
Tel: 39 0532 291176

Abstract

The iterative copper(I)-catalyzed cycloaddition (rt or microwave) between an ethynyl α-C-mannoside and alkyl 6-azido-α-C-mannoside derivatives was suited to the (1,6)-ligation between α-D-mannose units through 1,4-disubstituted triazole bridges, thus resulting in the formation of linear oligomers (80–90% yield) with alternating triazole and mannose fragments up to a triazolo-pentamannose derivative.

Graphical abstract: First synthesis of 1,2,3-triazolo-linked (1,6)-α-d-oligomannoses (triazolomannoses) by iterative Cu(i)-catalyzed alkyne–azide cycloaddition

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Article information

DOI
https://doi.org/10.1039/B609734K
Article type
Communication
Submitted
10 Jul 2006
Accepted
11 Jul 2006
First published
26 Jul 2006

Org. Biomol. Chem., 2006,4, 3225-3227

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First synthesis of 1,2,3-triazolo-linked (1,6)-α-D-oligomannoses (triazolomannoses) by iterative Cu(I)-catalyzed alkyne–azide cycloaddition

P. Cheshev, A. Marra and A. Dondoni, Org. Biomol. Chem., 2006, 4, 3225 DOI: 10.1039/B609734K

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