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Synthesis of Mono- and Disaccharide 4-[(ω-Sulfanylalkyl)oxy]benzoylhydrazones as Potential Glycoligands for Noble Metal Nanoparticles

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Abstract

A procedure has been developed for the synthesis of previously unknown aldose 4-[(ω-sulfanylalkyl) oxy]benzoylhydrazones (where alkyl is hexyl or decyl and aldoses are D-glucose, D-galactose, D-maltose, and D-lactose) that a repromising glycoligands for noble metal nanoparticles. According to the 1H and 13C NMR data, 4-[(ω-sulfanylalkyl)oxy]benzoylhydrazones derived from D-glucose, D-maltose, and D-lactose in crystal and in DMSO-d6 solution have exclusively the cyclic pyranose structure (α- and β-anomers). D-Galactose 4-[(ω-sulfanylalkyl)oxy]benzoylhydrazones in DMSO-d6 solution exist as tautomeric mixtures of cyclic pyranose and open-chain acylhydrazone structures.

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Authors and Affiliations

  1. Institute of Macromolecular Compounds, Russian Academy of Sciences, Bol’shoi pr. V.O. 31, St. Petersburg, 199004, Russia

    A. Yu. Ershov, A. A. Martynenkov & A. V. Yakimansky

  2. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. Yu. Ershov

  3. State Research Testing Institute of Military Medicine, Ministry of Defense of the Russian Federation, ul. Lesoparkovaya, 4, St. Petersburg, 195043, Russia

    I. V. Lagoda

  4. St. Petersburg State University, Universitetskaya nab. 7-9, St. Petersburg, 199034, Russia

    A. V. Yakimansky

Authors
  1. A. Yu. Ershov
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  2. A. A. Martynenkov
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  3. I. V. Lagoda
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  4. A. V. Yakimansky
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Correspondence to A. Yu. Ershov.

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Russian Text © A.Yu. Ershov, A.A. Martynenkov, I.V. Lagoda, A.V. Yakimansky, 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 2, pp. 301–308.

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Ershov, A.Y., Martynenkov, A.A., Lagoda, I.V. et al. Synthesis of Mono- and Disaccharide 4-[(ω-Sulfanylalkyl)oxy]benzoylhydrazones as Potential Glycoligands for Noble Metal Nanoparticles. Russ J Gen Chem 89, 292–299 (2019). https://doi.org/10.1134/S1070363219020208

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  • DOI: https://doi.org/10.1134/S1070363219020208

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