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Structure and Reactivity of Glycosides: IV. Koenigs-Knorr Synthesis of Aryl β-D-Glucopyranosides Using Phase-Transfer Catalysts

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Abstract

A series of acetylated aryl β-D-glucopyranosides were prepared in 12-63% yields from tetra-O- acetyl-α-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phasetransfer catalysts in glycosylation of phenols.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, St. Petersburg, Russia

    A. E. Pavlov, V. M. Sokolov & V. I. Zakharov

  2. Research and Production Association of Pulp-and-Paper Industry, St. Petersburg, Russia

    A. E. Pavlov, V. M. Sokolov & V. I. Zakharov

Authors
  1. A. E. Pavlov
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  2. V. M. Sokolov
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  3. V. I. Zakharov
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Pavlov, A.E., Sokolov, V.M. & Zakharov, V.I. Structure and Reactivity of Glycosides: IV. Koenigs-Knorr Synthesis of Aryl β-D-Glucopyranosides Using Phase-Transfer Catalysts. Russian Journal of General Chemistry 71, 1811–1814 (2001). https://doi.org/10.1023/A:1013971214679

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  • DOI: https://doi.org/10.1023/A:1013971214679

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