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

Vincent Aucagne (1) , Arnaud Tatibouët (1) , Patrick Rollin (1)

1 ICOA - Institut de Chimie Organique et Analytique

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.

Domaines: Sciences du Vivant [q-bio]

Vincent Aucagne, Arnaud Tatibouët, Patrick Rollin. Wittig approach to carbohydrate-derived vinyl sulfides, new substrates for regiocontrolled ring-closure reactions. Tetrahedron, 2004, 60 (8), pp.1817-1826. ⟨10.1016/j.tet.2003.12.040⟩. ⟨hal-02086021⟩