Solvent-controlled regioselective protection of 5'-O-protected thymidine.

Karine Teste (1) , Ludovic Colombeau (1) , Amel Hadj-Bouazza (1) , Rachida Zerrouki (1) , Romain Lucas (1) , Pierre Krausz (1) , Yves Champavier (2)

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

This paper describes an efficient procedure for selective 3'-O- or 3-N-protection of 5'-O-tert-butyldimethylsilylthymidine, depending on the use of aprotic polar solvents with low or high dielectric constant, respectively. These syntheses were activated by either ultrasound or microwaves. Several alkyl bromides offer a convenient route to prepare 3'-O- or 3-N-protected and functionalized thymidine derivatives.

Mots clés: Regioselective protection; Nucleoside; Solvent effect; Ultrasound activation; Microwave activation

Domaines: Chimie organique

Karine Teste, Ludovic Colombeau, Amel Hadj-Bouazza, Rachida Zerrouki, Romain Lucas, et al.. Solvent-controlled regioselective protection of 5'-O-protected thymidine.. Carbohydrate Research, 2008, 343 (9), pp.1490-5. ⟨10.1016/j.carres.2008.04.026⟩. ⟨hal-00686437⟩