SELENOXIDE ELIMINATION FOR THE SYNTHESIS OF UNSATURATED-SUGAR URACIL NUCLEOSIDES

被引:56
作者
HARAGUCHI, K [1 ]
TANAKA, H [1 ]
MAEDA, H [1 ]
ITOH, Y [1 ]
SAITO, S [1 ]
MIYASAKA, T [1 ]
机构
[1] SHOWA UNIV,SCH PHARMACEUT SCI,HATANODAI 1-5-8,SHINAGAWA KU,TOKYO 142,JAPAN
关键词
D O I
10.1021/jo00018a038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:5401 / 5408
页数:8
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