Tetrahedron letters

Reductive elimination of glycosyl phenyl sulfones by SmI 2-HMPA: A convenient synthesis of substituted pyranoid glycals

P de Pouilly, A Chénedé, JM Mallet, P Sinaÿ

Index: De Pouilly, Pierre; Chenede, Alain; Mallet, Jean-Maurice; Sinay, Pierre Tetrahedron Letters, 1992 , vol. 33, # 52 p. 8065 - 8068

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Citation Number: 59

Abstract

Abstract A series of substituted glycosyl phenyl sulfones was converted into glycals after reductive samariation with SmI 2 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.