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Nucleic Acids Symposium Series 2004 48(1):47-48; doi:10.1093/nass/48.1.47
© 2004 by Oxford University Press
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Stereoselective synthesis of 4'-carbon-substituted xylofuranosyladenines

Yutaka Kubota, Kazuhiro Haraguchi, Mayumi Kunikata, Mari Hayashi, Masaomi Ohkawa and Hiromichi Tanaka

School of Pharmaceutical Sciences, Showa University, 1-5-8 Hadanodai, Shinagawa-ku, Tokyo 142-8555, Japan

Epoxidation of 2',5'-bis-O-silyl-protected N6 pivaloyl-3',4'-unsaturated adenine nueleosides (1,2 and 3) with dimethyldioxirane uniformly proceeded face-selectively to give the respective 3',4'-ß-epoxides (4,5 and 6). Ring cleavage of these epoxides examined with Me3Al in CH2Cl2 showed that the TBDMS (4) or TES (5) protected epoxide gave the desired 4'-{alpha}-methylated product (8 or 10) as the major stereoisomer, while use of the TBDPS protected epoxide (6) resulted in reverse stereoselectivity. Reactions of 4 with other organoaluminum reagents were also carried out.


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