Synthesis of Thiodisaccharides by Ring Opening of Epoxides from Unsaturated Sugars

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

Whistler, British Columbia, Canadá

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. 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.