Synthesis of 2',3'-dideoxynucleoside phosphoesters using H-phosphonate chemistry on soluble polymer support |
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Authors: | Crauste Céline Périgaud Christian Peyrottes Suzanne |
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Affiliation: | UMR CNRS-UM1-UM2, IBMM, University Montpellier, France. |
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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. |
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