Reductive elimination of glycosyl phenyl sulfones by SmI2-HMPA: A convenient synthesis of substituted pyranoid glycals

Article abstract of DOI:10.1016/S0040-4039(00)74718-6

A series of substituted glycosyl phenyl sulfones was converted into glycals after reductive samariation with SmI₂ in the presence of hexamethylphosphoric triamide, followed by elimination of the substituent at C-2. Practically quantitative yields were obtained when the leaving group was an acetate, as illustrated here with seven substrates.