Synthesis of 2',-3'-Dideoxynucleoside Phosphoesters Using H-Phosphonates Chemistry on Soluble Polymer Support Auteur(s): Peyrottes S. (Article) Publié: European Journal Of Organic Chemistry, vol. 76 p.997-1000 (2011) Ref HAL: hal-00616748_v1 DOI: 10.1021/jo1022958 Résumé: Phosphorylation of ddC and 3TC was efficiently performed on soluble poly(ethylene glycol) support. The corresponding 5' -monophosphate derivatives were obtained by oxidation of the support bound 5' -H-phosphonate intermediates. Then, di- and triphosphorylations were carried out using a carbonyldiimidazole activation step followed by nucleophilic substitution with suitable phosphate salts. Trivalent phosphorus chemistry appeared as a good alternative for monophosphate synthesis of acid-sensitive 2',3' -dideoxynucleosides. |