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Glycosylation of 5-phenyl-1,3,4-oxadiazole-2-thiol with α-D-glucopyranosyl chloride under phase transfer conditions

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Abstract

5-Phenyl-1,3,4-oxadiazole-2-thiol is glycosylated easily and in high yields with 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride in the presence of catalytic amounts of aliphatic and aromatic crown ethers under phase transfer (solid-organic solvent) conditions. The reaction rate and the ratio of the resulting N-and S-regioisomers depend on the catalyst nature.

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Abbreviations

CE:

crown ether

References

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Authors and Affiliations

  1. Vernadsky Tauric National University, pr. Vernadskogo 4, Simferopol, Autonomous Republic of Crimea, 95007, Ukraine

    V. O. Kur’yanov, U. S. Priskoka, T. A. Chupakhina & V. Ya. Chirva

  2. Bogatsky Physicochemical Institute, National Academy of Sciences of Ukraine, Chemomorskaya doroga 86, Odessa, 270080, Ukraine

    S. A. Kotlar

Authors
  1. V. O. Kur’yanov
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  2. S. A. Kotlar
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  3. U. S. Priskoka
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  4. T. A. Chupakhina
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  5. V. Ya. Chirva
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Correspondence to V. O. Kur’yanov.

Additional information

Original Russian Text © V.O. Kur’yanov, S.A. Kotlar, U.S. Priskoka, T.A. Chupakhina, V.Ya. Chirva, 2006, published in Bioorganicheskaya Khimiya, 2006, Vol. 32, No. 5, pp. 520–523.

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Kur’yanov, V.O., Kotlar, S.A., Priskoka, U.S. et al. Glycosylation of 5-phenyl-1,3,4-oxadiazole-2-thiol with α-D-glucopyranosyl chloride under phase transfer conditions. Russ J Bioorg Chem 32, 468–471 (2006). https://doi.org/10.1134/S1068162006050098

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  • DOI: https://doi.org/10.1134/S1068162006050098

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