Towards α-or β-DC-glycosyl compounds by tin-catalyzed addition of glycosyl radicals to acrylonitrile and vinylphosphonate, and flexible reduction of tetra-O-acetyl-α-D …

JP Praly, AS Ardakani, I Bruyère, C Marie-Luce…

Index: Praly, Jean-Pierre; Ardakani, Azin Salek; Bruyere, Isabelle; Marie-Luce, Chrystelle; Bing Qin, Bing Carbohydrate Research, 2002 , vol. 337, # 18 p. 1623 - 1632

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Citation Number: 17

Abstract

Photo-induced radical addition of acetylated α-d-glucopyranosyl bromide (1) to acrylonitrile or diethyl vinylphosphonate, in the presence of catalytic amounts of tri-n-butyltin chloride and sodium (or tetra-n-butylammonium) cyanoborohydride in excess, allowed efficient preparations of α-configurated nonononitrile and 2-(α-d-glucopyranosyl)-ethylphosphonate (79, 70% yields, respectively). These conditions led to 2-(α-d-manno-, and ...