Functional group tolerance in organocatalytic regioselective acylation of carbohydrates.
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.
Ueda
Yoshihiro
Y
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Muramatsu
Wataru
W
Mishiro
Kenji
K
Furuta
Takumi
T
Kawabata
Takeo
T
D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008968:Molecular Conformation; D013237:Stereoisomerism
D002241:Carbohydrates