Microwave-assisted synthesis of a triazole-linked 3'-5' dithymidine using click chemistry.

Romain Lucas (1) , Virginie Neto (1) , Amel Hadj-Bouazza (1) , Rachida Zerrouki (1) , Robert Granet (1) , Pierre Krausz (1) , Yves Champavier (2)

1 LCSN - Laboratoire de Chimie des Substances Naturelles
2 RMN - Service Commun de Résonance Magnétique Nucléaire

Synthesis of a triazole-linked 3'-5' thymidine dimer making use of 1,3-dipolar cycloaddition is described. The azido-precursor was obtained by regioselective chlorination of thymidine, followed by azidation. The second precursor, a propargyl derivative, was obtained by selective 3'-O-alkylation of thymidine. Two 'click systems' were compared to obtain the desired dimer. These reactions were performed by microwave irradiation.

Domaines: Chimie organique

Romain Lucas, Virginie Neto, Amel Hadj-Bouazza, Rachida Zerrouki, Robert Granet, et al.. Microwave-assisted synthesis of a triazole-linked 3'-5' dithymidine using click chemistry.. Tetrahedron Letters, 2008, 49 (6), pp.1004-1007. ⟨hal-00686734⟩