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

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.

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