A regiospecific synthesis of unsaturated nucleosides, carbohydrates and other olefins

Abstract

Vicinal disubstituted nucleosides, carbohydrates and cyclohexane derivatives with a pair of radical leaving groups, such as chloro, bromo, phenoxythiocarbonyloxy, and imidazolylthiocarbonyloxy groups, have been successfully converted to the corresponding olefins in high yields (60–90%) without observed side products, by reaction with tri-n-butyltin hydride and azobisisobutyronitrile in an appropriate solvent.