Studies on the Synthesis of Novel Carbohydrates with Sulfur in the Ring. Part III. The Synthesis of Derivatives of 2,6-Dithio-hex-4-en-2-ulopyranosidononitriles

Abstract

The cis-hydroxylation of 3,6-dihydro-3-methoxy-2-methylthio-2H-thiopyran-2-carbonitrile and of 3-exo-cyano-3-methylthio-2-thiabicyclo[2.2.1]hept-5-ene by treatment with OsO4–pyridine afforded sulfur analogs of two new types of carbohydrates. The Diels–Alder reaction of trans,trans,-l,4-diacetoxy-l,3-butadiene with methyl cyanodithioformate gave a one-step synthesis of methyl 3,6-di-O-acetyl-4,5-dideoxy-2,6-dithio-α-DL-threo-hex-4-en-2-ulopyranosidononitrile.