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Aucagne, V ; Tatibouet, A ; Rollin, P

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

Tetrahedron 60 (8) 1817-1826

par Administrateur - publié le

Abstract :

Reaction of methyl- and phenylthiomethylidene phosphoranes 1 and 2 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. (C) 2004 Elsevier Ltd. All rights reserved.