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Note | Regular issue | Vol 65, No. 12, 2005, pp.2991-2999
Published online, 14th October, 2005
DOI: 10.3987/COM-05-10551
Chemical Modification of the Sugar Moiety of Pyrimidine Nucleosides via a 4’,5’-Epoxyuridine Intermediate

Hideki Takasu, Hironao Sajiki,* and Kosaku Hirota*

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

Abstract

The reaction of 4’,5’-unsaturated nucleoside (5) with m-CPBA provided different products depending on the solvent. 4’,5’-Epoxynucleoside (6) was generated as a key intermediate although 6 was not stable enough to isolate and further reaction progressed. When the reaction was performed in CH2Cl2, 2,4’-cyclonucleoside (7) and 4’-ketonucleoside (8) were obtained. On the other hand, 4’-alkoxy derivatives (9 and 11) together with their epimers (10 and 12) were aquired as a mixture by the nucleophilic attack of alcohol.