Bulletin of the Chemical Society of Japan p. 239 - 242 (1982)
Update date:2022-08-11
Topics:
Sekine, Mitsuo
Mori, Hiroyuki
Hata, Tsujiaki
Nucleoside ethoxycarbonylphosphonates were prepared by condensation of appropriately protected nucleosides with ethoxycarbonylphosphonic acid.They were easily converted by treatment with 1 M NaOH followed by trimethylsilylation to highly reactive bis(trimethylsilyl) nucleoside phosphite intermediates which were allowed in situ to react with water, diphenyl disulfide, 2,2'-dipyridyl disulfide, and aldehydes to afford the corresponding nucleoside phosphonates, nucleoside S-phenyl phosphorothioates, nucleoside phosphates, and nucleoside α-hydroxy phosphonates in good yields, respectively.The nucleoside phosphonates were further converted to nucleosides under mild acidic conditions.Thus, the ethoxycarbonyl group proved to serve as a versatile protecting group for not only H-P(O) but also HO-P(O) and hydroxy groups of sugars.
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