title: Regioselective monoacylation of 2-O-α-D-glucopyranosyl-L-ascorbic acid by a polymer catalyst in N,N-dimethylformamide.
abstract: 6-O-Dodecanoyl-2-O-α-D-glucopyranosyl-L-ascorbic acid (6-sDode-AA-2G) was synthesized from 2-O-α-D-glucopyranosyl-L-ascorbic acid and lauric anhydride with a polymer catalyst, poly(4-vinylpyridine), in N,N-dimethylformamide without the introduction of protecting groups. The optimum reaction conditions enabled 6-sDode-AA-2G to be synthesized in a yield of 49.7%. The yield and the regioselectivity in this method were far superior to those in our previous method by using an enzyme. The polymer catalyst could be recycled more than five times without any significant activity loss.
authors: Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, Shobara, Hiroshima 727-0023, Japan. atai@pu-hiroshima.ac.jp
authors: Akihiro
authors: A
authors: Tai
authors: Yuji
authors: Y
authors: Iwaoka
authors: Hideyuki
authors: H
authors: Ito
mesh_terms: D000215:Acylation; D000812:Anhydrides / Q000737:chemistry; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D004126:Dimethylformamide; D005559:Formamides / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis*; D007700:Kinetics; D007850:Lauric Acids / Q000737:chemistry; D011145:Polyvinyls / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D000812:Anhydrides; D005559:Formamides; D005960:Glucosides; D007850:Lauric Acids; D011145:Polyvinyls; D012997:Solvents; C030358:lauric acid; C019535:poly(4-vinylpyridine); C065378:ascorbic acid 2-O-glucoside; D004126:Dimethylformamide; D001205:Ascorbic Acid