Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates

摘要

Organocatalytic regioselective acylation of mono- anddisaccaharides with various functionalized acid anhydrideshas been developed. Acylation of octyl fi-a-glucopyrano-side with acid anhydrides derived from a-amino acids,cinnamic acid, and gallic acid took place at C(4)-OH with67-94% regioselectivity in the presence of catalyst 1.Regioselective acylation of disaccharides with functiona-lized acid anhydrides was also achieved with 78-94%selectivity. Especially, a disaccharide with seven freehydroxy groups (X = OH, = H) underwent acylationat C(4)-OH with 78% regioselectivity in the presence of 1.Thus, functional group tolerance in the regioselectiveacylation catalyzed by 1 was found to be high.