Reaction of the 2'-silyl and 2'-stannyl derivatives of 6-(bromomethyl)dimethylsilyl-1',2'-unsaturated uridine under radical conditions.
The mode of cyclization (5-exo versus 6-endo) of 2-sila-5-hexen-1-yl radicals generated from 2'-tributylstannyl- and 2'-trimethylsilyl-6-(bromomethyl)dimethylsilyl-1',2'-unsaturated uridines (8 and 9) was investigated. Although the actual structure of the reaction products differ from each other reflecting the ease of elimination of the 2'-substituent, it was found that both substrates prefer the 5-exo-cyclization pathway.
Ogamino
Junko
J
School of Pharmaceutical Sciences, Showa University, Shinagawa-ku, Tokyo, Japan.
Mizunuma
Hideaki
H
Kumamoto
Hiroki
H
Haraguchi
Kazuhiro
K
Tanaka
Hiromichi
H
D009947:Organotin Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D009947:Organotin Compounds; D012821:Silanes; D014529:Uridine