A novel method for the synthesis of 4'-thiopyrimidine nucleosides using hypervalent iodine compounds.
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.
Nishizono
Naozumi
N
Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan. nishizon@hoku-iryo-u.ac.jp
Baba
Ryosuke
R
Nakamura
Chika
C
Oda
Kazuaki
K
Machida
Minoru
M
D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013872:Thionucleosides / Q000138:chemical synthesis*
D011741:Pyrimidine Nucleosides; D013872:Thionucleosides; D007455:Iodine