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

Citation:

Gimisis T, Ialongo G, Zamboni M, Chatgilialoglu C. {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 Lett. 1995;36:6781–6784.

Abstract:

A number of nucleoside substrates has been reduced under free radical conditions with tris(trimethylsilyl)silane. In one case a novel type of a beta-(acyloxy)alkyl radical rearrangement has been observed, which leads through the generation of a C-1' radical species to the stereoselective preparation of an alpha-ribonucleoside. The rate of the above 12-migration has been estimated, and a comparison with previously reported results has been made.