Tetrahedron

Wittig approach to carbohydrate-derived vinyl sulfides, new substrates for regiocontrolled ring-closure reactions

V Aucagne, A Tatibouët, P Rollin

Index: Aucagne, Vincent; Tatibouet, Arnaud; Rollin, Patrick Tetrahedron, 2004 , vol. 60, # 8 p. 1817 - 1826

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Citation Number: 39

Abstract

Reaction of methyl-and phenylthiomethylidene phosphoranes and with a variety of reducing sugars has been explored. Furano-type carbohydrates afforded with good yields the corresponding open-chain vinyl sulfides, whereas pyrano derivatives produced elimination compounds together with the expected vinyl sulfides, depending on the nature of the protective groups.