RADICAL TRANSFORMATIONS OF NUCLEOSIDES WITH (ME(3)SI)(3)SIH - GENERATION OF A C-1' RADICAL THROUGH 1,2-MIGRATION OF AN ACYLOXY GROUP

Authors
GIMISIS T IALONGO G ZAMBONI M CHATGILIALOGLU C
Citation
T. Gimisis et al., RADICAL TRANSFORMATIONS OF NUCLEOSIDES WITH (ME(3)SI)(3)SIH - GENERATION OF A C-1' RADICAL THROUGH 1,2-MIGRATION OF AN ACYLOXY GROUP, Tetrahedron letters, 36(37), 1995, pp. 6781-6784
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
37
Year of publication
1995
Pages
6781 - 6784
Database
ISI
SICI code
0040-4039(1995)36:37<6781:RTONW(>2.0.ZU;2-M
Abstract
A number of nucleoside substrates has been reduced under free radical conditions with tris(trimethylsilyl)silane. In one case a novel type o f a beta-(acyloxy)alkyl radical rearrangement has been observed, which leads through the generation of a C-1' radical species to the stereos elective preparation of an alpha-ribonucleoside. The rate of the above 12-migration has been estimated, and a comparison with previously rep orted results has been made.