Ring opening of 4',5'-epoxynucleosides: a novel stereoselective entry to 4'-C-branched nucleosides.
Stereoselective synthesis of 4'-alpha-carbon-substituted nucleosides has been accomplished through epoxidation of 4',5'-unsaturated nucleosides with dimethyldioxirane (DMDO) and successive SnCl(4)-promoted ring opening of the resulting 4',5'-epoxynucleosides with organosilicon reagents. [reaction: see text]
Haraguchi
Kazuhiro
K
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. harakazu@pharm.showa-u.ac.jp
Takeda
Shingo
S
Tanaka
Hiromichi
H
D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry; D009947:Organotin Compounds / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D009705:Nucleosides; D017646:Organosilicon Compounds; D009947:Organotin Compounds; C064455:dimethyldioxirane