title: Synthesis of 2',3'-dideoxynucleoside phosphoesters using H-phosphonate chemistry on soluble polymer support.
abstract: 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.
authors.affiliation: UMR CNRS-UM1-UM2, IBMM, University Montpellier, France.
authors.forename: Céline
authors.initials: C
authors.lastname: Crauste
authors.forename: Christian
authors.initials: C
authors.lastname: Périgaud
authors.forename: Suzanne
authors.initials: S
authors.lastname: Peyrottes
mesh_terms: D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010766:Phosphorylation; D011108:Polymers / Q000737:chemistry*; D012995:Solubility
chemical_list: D015224:Dideoxynucleosides; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D011108:Polymers