ChemInform Abstract: Branched-Chain Sugars as Push-Pull Butadienes

Treatment of methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside (2) with 3-benzyl-2-methylthio-2-thiazolinium iodide (3), 4,5-dihydro-3-methyl-2-methylthio-1,3-thiazinium iodide (5) and 3-benzyl-4,5-dihydro-2-methylthio-1,3-thiazinium iodide (6), respectively, gave methyl 4,6-O-benzylidene-3-[(2Z)-3-benzyl-2-thiazolidinylidene, 3-methyl-1,3-thiazinan-2-ylidene and 3-benzyl-1,3-thiazinan-2-ylidene]-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside (4), (7), (8), respectively.