Nucleosides and nucleotides. 134. Synthesis of 2′-C-alkynyl-2′-deoxy-1-β- D-arabinofuranosylpyrimidines via radical deoxygenation of tert-propargyl alcohols in the sugar moiety

Article abstract of DOI:10.1016/S0040-4020(01)89580-6

Synthesis of 2′-deoxy-2′-C-ethynyl-1-β-D-arabinofuranosyluracil (8c), -thymine (8f), and -cytosine (11) has been done by stereo specific radical deoxygenation of the corresponding 2′-tert-TMSpropargyl methoxalyl esters with Bu₃SnH in the presence of AIBN. 2′-Deoxy-2′-C-hexynyl derivative 8d was also prepared under similar conditions. On the other hand, the deoxygenation of the phenylpropargyl or propargyl esters gave complex mixtures due to hydrostannylation of the triple bonds.