APPLICATION OF THE KECK RADICAL COUPLING REACTION TO THE PREPARATION OF ALLYLATED C5 FURANOSIDES AND C6 PYRANOSIDES

Allylated C5 furanosides and C6 pyranosides were prepared from known monosaccharide diol oi polyol derivatives via a reaction sequence involving the initial selective formation of the primary iodide followed by application of the Keck allyl radical coupling reaction. Although the yield's of the products in the coupling reaction were somewhat modest (usually 55-65%), the protocol was applicable to a variety of substrates, including sterically crowded cases, is experimentally simple and suitable for large scale preparations.