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
- 1 May 1975
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 53 (9) , 1362-1366
- https://doi.org/10.1139/v75-188
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.Keywords
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