The Use of Grignard Reagents in Carbohydrate Synthesis. The Synthesis of Branched-chain Deoxy Sugars and Their Anomerizations

Article abstract of DOI:10.1246/bcsj.56.1095

The reactions of methyl 5-O-benzyl-2-O- and -3-O-tosyl-β-D-ribofuranosides with methylmagnesium iodide gave, in one-step, 2-deoxy-3-C- and 3-deoxy-2-C-methyl branched-chain sugars, respectively. These sugars were anomerized with Grignard reagents; the thermodynamically more stable anomers were converted preferentially into the respective less stable anomers.