Issue 21, 2009
From the journal:

Organic & Biomolecular Chemistry

Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition†

Sonia Amel Diab,a   Antje Hienzch,a   Cyril Lebargy,a   Stéphane Guillarme,a   Emmanuel Pfunda  and  Thierry Lequeux*a  

* Corresponding authors

a Laboratoire de Chimie Moléculaire et Thioorganique, ENSICAEN, Université de Caen Basse-Normandie, UMR-CNRS 6507, FR3038, 6 Bd du Maréchal Juin, Caen Cedex, France
E-mail: thierry.lequeux@ensicaen.fr
Fax: +33 231452865
Tel: +33 231452854

Abstract

Preparation of several acyclonucleosides containing both a difluoromethylphosphonate group and a triazole moiety is described starting from a difluorophosphonosulfide. The key step of the synthesis involves a copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition between difluorophosphonylated azides and propargylated nucleobases derived from thymine and 2-amino-6-chloropurine.

Graphical abstract: Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition

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Article information

DOI
https://doi.org/10.1039/B912724K
Article type
Paper
Submitted
29 Jun 2009
Accepted
27 Jul 2009
First published
21 Aug 2009

Org. Biomol. Chem., 2009,7, 4481-4490

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Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition

S. Amel Diab, A. Hienzch, C. Lebargy, S. Guillarme, E. Pfund and T. Lequeux, Org. Biomol. Chem., 2009, 7, 4481 DOI: 10.1039/B912724K

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