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Note | Special issue | Vol 67, No. 1, 2006, pp.399-405
Published online, 15th July, 2005
DOI: 10.3987/COM-05-S(T)14
Formation of 4’,5’-Didehydro-5’-deoxy-3’-O-methyluridine via Regioselective Nucleophilic Addition of Methoxide Anion to 2’,3’-Anhydro-5’-dehydro-5’-iodouridine

Hironao Sajiki,* Hideki Takasu, and Kosaku Hirota*

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

Abstract

Treatment of 2’,3’-anhydro-5’-deoxy-5’-iodouracil (1) with sodium methoxide regioselectively provided 4’,5’-didehydro-5’-deoxy-3’-O-methyluridine (2) as the sole product via 4’,5’-didehydro-5’-deoxy-2’,3’-epoxyuridine (6) as an intermediate.