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- A facile and effective synthesis of lamivudine 5'-diphosphate doi link

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.