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Specific features of phase transfer catalytic glycosylation of aromatic hydroxy acids

Abstract

Reactions of peracetylated α-D-glucosaminyl chloride with isomeric hydroxybenzoic and 1-hydroxy-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 temperatures affected the reaction composition and product yields. The O-β-glycosyl esters of ortho-hydroxyaromatic 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-carboxyphenylglucosaminide were comparable with that of aspirin.

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Abbreviations

15C5:

15-crown-5

PT:

phase transfer

[3.3] DB18C6:

[3.3]-dibenzo-18-crown-6

PTC:

phase transfer catalysis

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Correspondence to V. O. Kuryanov.

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Original Russian Text © T.A. Chupakhina, A.A. Astrakhantseva, V.O. Kuryanov, 2013, published in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 3, pp. 346–352.

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Chupakhina, T.A., Astrakhantseva, A.A. & Kuryanov, V.O. Specific features of phase transfer catalytic glycosylation of aromatic hydroxy acids. Russ J Bioorg Chem 39, 306–311 (2013). https://doi.org/10.1134/S1068162013030059

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  • DOI: https://doi.org/10.1134/S1068162013030059

Keywords

  • analgesic activity
  • aromatic hydroxy acids
  • crown ether
  • glucosaminides
  • glycosyl ester
  • glycosylation
  • phase transfer catalysis