Synthesis of aryl-2-deoxy-d-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides Original Research Article

The synthesis of either anomers of aryl 2-deoxy-d-glycopyranosides from 2-deoxy-1-thioglycosides is reported. The α-anomers form as the major product when thioglycosides react with differently substituted phenols and naphthols, in the presence of N-iodosuccinimide/triflic acid. On the other hand, reaction of the thioglycosides with bromine initially, followed by reaction with aryloxy anions lead to aryl 2-deoxy-β-d-glycosides with high specificities.