A facile and effective synthesis of lamivudine 5'-diphosphate Auteur(s): Perigaud C. (Article) Publié: Tetrahedron Letters, vol. 52 p.1250-1252 (2011) Ref HAL: hal-00566611_v1 DOI: 10.1016/j.tetlet2010.12.105 Résumé: We report on the first solution synthesis of lamivudine 5'-diphosphate in both high yield and purity. Efficient synthesis of lamivudine 5'-monophosphate was obtained through lamivudine H-phosphonate oxydation by (-)-(8,8-dichlorocamphorylsulfonyl)oxaridine. Diphosphorylation was performed by nucleophilic substitution of the phosphorimidazolate derivative of lamivudine HPLC coupled with UV or MS detection was found to be an invaluable tool for the follow-up of phosphorylation reactions. |