Tetrahedron letters

Versatile use of bis-cyclic thionocarbonates of polyols as bis-electrophilic intermediates. Synthesis of polyhydroxylated thioanhydropentitols with d, l-arabino, l-ribo …

A Danquigny, M Benazza, S Protois, G Demailly

Index: Danquigny, Alain; Benazza, Mohammed; Protois, Sylvain; Demailly, Gilles Tetrahedron Letters, 2004 , vol. 45, # 22 p. 4365 - 4369

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Citation Number: 7

Abstract

1-O-Benzylpentitols (with d-arabino, d-lyxo, d, l-xylo and d, l-ribo configurations) and aldose dibenzyldithioacetals (with l-arabino, d-lyxo, d-xylo, d-ribo, d-galacto, d-gluco and d-manno configurations) were directly and efficiently transformed into their cyclic bis-thionocarbonate derivatives (61–73%) by reaction with diimidazolyl thione (Im2CS) in 1, 4-dioxane. These bis- electrophilic adducts react regioselectively with Na2S· 9H2O to lead to 1, 4-, 2, 5-or 3, 6- ...