A novel synthesis of AZT

Christine Gauthier (1) , Yvan Ramondenc (2) , Gérard Plé (2)

1 IRCOF - Institut de Chimie Organique Fine
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

A novel synthesis of AZT has been achieved from two commercial available products acetaldehyde and d-mannitol. The originality of the synthesis consists of using the powerful monovinylogation reagent, the 2-lithio-1-trimethylsiloxyethylene, and to introduce the thymine moiety and to build the furanose ring in the same and last step.

Mots clés: nucleosides; cyclisation; azides; antivirals

Domaines: Chimie; Catalyse; Matériaux; Chimie organique

Christine Gauthier, Yvan Ramondenc, Gérard Plé. A novel synthesis of AZT. Tetrahedron, 2001, 57 (35), pp.7513-7517. ⟨10.1016/S0040-4020(01)00695-0⟩. ⟨hal-02385788⟩