Journal of Organic Chemistry p. 5401 - 5408 (1991)
Update date:2022-08-04
Topics:
Haraguchi, Kazuhiro
Tanaka, Hiromichi
Maeda, Hideaki
Itoh, Yoshiharu
Saito, Shigeru
Miyasaka, Tadashi
Introduction of a phenylseleno group to the sugar portion of uracil nucleosides and selenoxide elimination reactions of the resulting selenium-containing derivatives are described.A phenylselenide anion prepared by reducing (PhSe)2 with LiAlH4 was found to be highly reactive.By using this selenide as a nucleophile, ring openings of various types of cyclonucleosides and nucleosides having an anhydro structure in the sugar portion were accomplished.The products, which contain a phenylseleno group in the sugar portion, were oxidized with m-CPBA in CH2Cl2, and their susceptibility to the selenoxide elimination and regiochemistry of the reaction was investigated.
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