Expeditious preparation of 1,6-anhydro-1-thio-ß-d-hexopyranose derivatives.

A convenient reaction condition has been developed for the preparation of 1,6-anhydro-1-thio-ß-d-glycopyranose derivatives in excellent yield. The reaction condition is significantly fast, clean and can be scaled up for its use in the organic synthesis.

Selective acetolysis of primary benzyl groups in carbohydrate derivatives under the mild reaction condition.

Selective acetolysis of the primary benzyloxy groups in a wide variety of carbohydrate derivatives was achieved in excellent yield using acetic anhydride and perchloric acid supported over silica (HClO4-SiO2) as a solid acid catalyst in a fast reaction condition without using any organic solvent. The reaction condition is significantly rapid and can be scaled up for its use in the multi-step oligosaccharide synthesis.

Organocatalyzed preparation of 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives.

Organocatalytic coupling of glycosyl azides with enolates of active ketones and esters through azide-enolate [3 + 2] cycloaddition in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) furnished 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives in excellent yield. The reaction condition is simple and can be scaled-up. Graphical abstract Coupling of glycosyl azides with active ketones through azide-enolate [3 + 2] cycloaddition in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) furnished 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives in excellent yield.