Selenoxide Elimination for the Synthesis of Unsaturated-Sugar Uracil Nucleosides

DOI: 10.1021/jo00018a038

Source and publish data:

Journal of Organic Chemistry p. 5401 - 5408 (1991)

Update date:2022-08-04

Topics:

Authors:

Haraguchi, Kazuhiro

Tanaka, Hiromichi

Maeda, Hideaki

Itoh, Yoshiharu

Saito, Shigeru

Miyasaka, Tadashi

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Article abstract of DOI:10.1021/jo00018a038

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.

Full text of DOI:10.1021/jo00018a038

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