Stereo-controlled C-C bond formation at the anomeric position of uracil nucleosides.
Stereoselective synthesis of 1'-carbon-substituted uracil nucleosides has been achieved through face-selective bromo-pivaloyloxylation of a 1',2'-unsaturated derivative and successive SnCl4-promoted nucleophilic substitution with organosilicon reagents. This constitutes the first example of C-C bond formation at the anomeric position of nucleosides.
Haraguchi
K
K
School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
Itoh
Y
Y
Tanaka
H
H
Miyasaka
T
T
D002244:Carbon / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014498:Uracil / Q000737:chemistry*
D009705:Nucleosides; D017646:Organosilicon Compounds; D014498:Uracil; D002244:Carbon