Tetrahedron Letters 2015-12-01

Synthesis of _-triphosphotriester pronucleotides.

Yousef Beni, Chandravanu Dash, Keykavous Parang

Index: Tetrahedron Lett. 56(17) , 2247-2250, (2015)

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Abstract

Dinucleoside phosphorochloridite were synthesized from phosphorus trichloride and three nucleoside analogues, 3'-fluoro-2',3'-dideoxythymidine (FLT), 2',3'-dideoxy-5-fluoro-3'-thiacytidine (FTC), and 2',3'-dideoxy-3'-thiacytidine (3TC), in a multistep synthesis. Polymer-bound N-Boc p-acetoxybenzyl 5'-O-2'-deoxythymidine was reacted with dinucleoside phosphorochloridite in the presence of 2,6-lutidine, followed by the reaction with dodecyl alcohol and 5-(ethylthio)-1H-tetrazole, oxidation with tert-butyl hydroperoxide, and acidic cleavage, respectively, to afford the _-triphosphotriester derivatives containing three different nucleosides.