Tetrahedron

Synthesis of carbon-bridged 8, 5'-cyclopurine nucleosides: Nucleosides and nucleotides—XXIV11Part XXIII, T. Ueda, M. Yamamoto, A. Yamane, M. Imazawa and H. …

A Matsuda, M Tezuka, K Niizuma, E Sugiyama, T Ueda

Index: Matsuda,A. et al. Tetrahedron, 1978 , vol. 34, p. 2633 - 2637

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Citation Number: 38

Abstract

Treatment of 2', 3'-O-isopropylidene-5'-deoxy-8, 5'-cycloadenosine with selenium oxide afforded the 5'-oxo-compound. Reduction of the product with sodium borohydride proceeded stereoselectively to give the 8, 5'(S)-cycloadenosine. The 5'-R-isomer was obtained by the inversion of the 5'-OH group of the S-epimer via the mesyloxy derivative. Hydrolytic deamination of 8, 5'-cycloadenosines gave the inosine counterparts. Photo- ...