Nucleoside hydroxyphosphonates

Synthesis of nucleoside hydroxyphosphonates To a solution of diethyl H-phosphonate (0.75 mL, 8.2mmol) in THE (lOmL) at... 

Nucleoside Pyrophosphonates. Rosenberg et al. have reported that treatment of the geminal hydroxyphosphonate moiety of 2 -thymidine-3 -C-phosphonate with acetic anhydride yielded the phosphonate anhydride derivative (85a), the cyclic dinucleoside diphosphonate (85b) and the tetranucleoside diphosphonate (85c). ... 

Nucleoside oc-Hydroxyphosphonates. In recent years, there has been a tremendous resurgence of interest in synthesis of modified nucleosides, primarily because of their potential antiviral activity. Three modified nucleosides, 3 -azidothymidine [210], dideoxyinosine [211], and dideoxycytidine [212], are the only drugs of recognized therapeutic value in the treatment of AIDS. Their toxic side effects [213], which limited the application of these compounds, are the driving force to develop new nucleoside derivatives with the potential to be more selective anti-HIV agents. 

Szymahska A, Szymczak M, Boryski J et al (2006) Aryl nucleoside ff-phosphonates. Part 15 synthesis, properties and, anti-HIV activity of aryl nucleoside 5 -a-hydroxyphosphonates. Bioorg Med Chem 14 1924—1934... 

SCHEME 47.10. Synthesis of 5 -hydroxyphosphonate nucleoside analogs via stereoselective addition of diethyl H-phosphonate to aldehydes. 

McEldoon WL, Lee K, Wiemer DF. Synthesis of nucleoside a-hydroxyphosphonates. Tetrahedron Lett. 1993 34 5843-5846. 

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