title: Functional group tolerance in organocatalytic regioselective acylation of carbohydrates.
abstract: Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R' = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by 1 was found to be high.
authors.affiliation: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Ueda
authors.forename: Wataru
authors.initials: W
authors.lastname: Muramatsu
authors.forename: Kenji
authors.initials: K
authors.lastname: Mishiro
authors.forename: Takumi
authors.initials: T
authors.lastname: Furuta
authors.forename: Takeo
authors.initials: T
authors.lastname: Kawabata
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates