Synthesis of Thiodisaccharides by Ring Opening of Epoxides from Unsaturated Sugars

VARELA, O.; MANZANO, V. E.; UHRIG, M. L.

Whistler, British Columbia, Canada

Simposio; XXIIIrd International Carbohydrate Symposium; 2006

International Carbohydrate Organization

Thiodisaccharides are considered useful tools in inhibition studies of glycoside hydrolases due to their high stability in comparison to their naturally occurring counterparts. We have reported a straightforward synthesis of 3-deoxy-4-thiodisaccharides by reaction of sugar-derived  dihydropyranones with isothiouronium salts of aldoses. We describe here the epoxidation of unsaturated derivatives of sugars and the opening of the oxirane ring by 1-thioaldoses as an approach for the construction of the interglycosidic linkage of thiodisaccharides.