Synthesis of 2′,3′-Dideoxynucleoside Phosphoesters Using H-Phosphonate Chemistry on Soluble Polymer Support
- 30 December 2010
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (3), 997-1000
- https://doi.org/10.1021/jo1022958
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.Keywords
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