Regioselective Dehydration of Sugar Thioacetals under Mild Conditions

Sugars are abundant in waste biomass, making them sustainable chiral building blocks for organic synthesis. The demand for chiral saturated heterocyclic rings for pharmaceutical applications is increasing as they provide well-defined three-dimensional frameworks that show increased metabolic resistance. A range of sugar thioacetals can be dehydrated selectively at C-2 under mild basic conditions, and the resulting ketene thioacetals can be applied to the production of useful chiral building blocks via further selective dehydration reactions.

Automated summary

Sugars in waste biomass are sustainable chiral building blocks for organic synthesis, especially for pharmaceutical applications of chiral saturated heterocyclic rings. A range of sugar thioacetals can be selectively dehydrated at C-2 under mild basic conditions, and the resulting ketene thioacetals can be used for the production of useful chiral building blocks through further selective dehydration reactions.