Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides
Somak Paul1, Narayanaswamy Jayaraman
1Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
Abstract:
The synthesis of either anomers of aryl 2-deoxy-D-glycopyranosides from 2-deoxy-1-thioglycosides is reported. The alpha-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-beta-D-glycosides with high specificities.
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