title: Modification of the sugar moiety in uridine via 2',3'-epoxyuridine derivatives.
abstract: 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.
authors.affiliation: Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan.
authors.forename: Hideki
authors.initials: H
authors.lastname: Takasu
authors.forename: Yoshie
authors.initials: Y
authors.lastname: Tsuji
authors.forename: Hironao
authors.initials: H
authors.lastname: Sajiki
authors.forename: Kosaku
authors.initials: K
authors.lastname: Hirota
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D014529:Uridine / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D004852:Epoxy Compounds; D014529:Uridine