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Nucleic Acids Symposium Series 2004 48(1):49-50; doi:10.1093/nass/48.1.49
© 2004 by Oxford University Press
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Modification of the sugar moiety in uridine via 2',3'-epoxyuridine derivatives

Hideki Takasu, Yoshie Tsuji, Hironao Sajiki and Kosaku Hirota

Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan

The reaction of 5'-O-mesyl-2',3'-epoxyuridine or 5'-Oiodo-2',3'-epoxyuridine with a nucleophile gave 2'- and 3'-adducts as a mixture while the use of 4',5'-didehydro-5'-deoxy-2',3'-epoxyuridine as a substrate gave 4',5'-didehydro-5'-deoxy 3'-substituted derivatives as a main product. The slow N3 rearrangement reaction of the 3'-N3 adduct of 4',5'-didehydro-5'-deoxy-2',3'-epoxyuridine to the 5'-N3 adduct was observed in DMSO-d6.


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