title: A novel method for the synthesis of 4'-thiopyrimidine nucleosides using hypervalent iodine compounds.
abstract: The coupling reactions of cyclic sulfides with a silylated pyrimidine nucleobase using a hypervalent iodine reagent were investigated. The reaction of silylated uracil with cyclic sulfide 12 using PhI=O gave the desired beta-anomer 14 in moderate yield. 4'-Thiouridine (22) was obtained by deprotection of 14.
authors.affiliation: Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan. nishizon@hoku-iryo-u.ac.jp
authors.forename: Naozumi
authors.initials: N
authors.lastname: Nishizono
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Baba
authors.forename: Chika
authors.initials: C
authors.lastname: Nakamura
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Oda
authors.forename: Minoru
authors.initials: M
authors.lastname: Machida
mesh_terms: D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013872:Thionucleosides / Q000138:chemical synthesis*
chemical_list: D011741:Pyrimidine Nucleosides; D013872:Thionucleosides; D007455:Iodine