Carbohydrate Research 2011-11-08

Regioselective monoacylation of 2-O-α-D-glucopyranosyl-L-ascorbic acid by a polymer catalyst in N,N-dimethylformamide.

Akihiro Tai, Yuji Iwaoka, Hideyuki Ito

Index: Carbohydr. Res. 346(15) , 2511-4, (2011)

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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.Copyright © 2011 Elsevier Ltd. All rights reserved.