Specific Features of Phase Transfer Catalytic Glycosylation
of Aromatic Hydroxy Acids

T. A. Chupakhina, A. A. Astrakhantseva, and V. O. Kuryanov¹

Vernadsky Tauric National University, pr. Akademika Vernadskogo 4, Simferopol 95007, Ukraine

Received July 3, 2012; in final form, December 6, 2012

Abstract—Reactions of peracetylated -D-glucosaminyl chloride with isomeric hydroxybenzoic and
1hydroxy-2-naphthoic acids in a solid phase transfer system of potassium carbonate–acetonitrile were studied.
It was found that the nature of carboxylic acids, lipophilicity of the phase transfer catalyst, and reaction tem-
peratures affected the reaction composition and product yields. The O--glycosyl esters of ortho-hydroxyaro-
matic acids were first found to form anomeric 1,2-cis derivatives in the presence of potassium carbonate. The
structures of the synthesized compounds were confirmed by ¹H NMR spectroscopy. As was shown in vivo
experiments, the analgesic activities of glycosyl esters of salicylic acid and peracetylated 2-carboxyphenylglu-
cosaminide were comparable with that of aspirin.

Keywords: analgesic activity, aromatic hydroxy acids, crown ether, glucosaminides, glycosyl ester, glycosyla-
tion, phase transfer catalysis

DOI: 10.1134/S1068162013030059

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