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Communication | Regular issue | Vol 34, No. 4, 1992, pp.657-661
Published online, 1st January, 1970
DOI: 10.3987/COM-92-9570
Nucleosides and Nucleotides. 110. [2,3]-Sigmatropic Rearrangement of the Allylic Selenides to Allylic Amines in Sugar Moiety of Pyrimidine Nucleosides: Synthesis of 3'-Amino-2',3'-dideoxy-2'-methylidenecytidine

Abdalla Alsyed A. Hassan and Akira Matsuda*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060, Japan

Abstract

An allylic alcohol system in 2'-deoxy-2'-methylideneuridine derivative (4) was converted into the allylic selenide, 2',3'-didehydro-2',3'-dideoxy-2'-phenylselenomethyl derivative (11), which was treated with NCS and tert-butyl carbamate to afford a [2,3]-sigmatropic rearrangement product (13). Transformation of the uracil moiety of 13 into cytosine provided access to the title compound (16).