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Reaction of several resveratrol glycoside derivatives with hypochlorites in various media

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Chemistry of Natural Compounds Aims and scope

The reactions of pterostilbenoside (trans-3,5-dimethoxystilben-4′-O-β-D-glucoside) and Ar–O–Tr derivatives of resveratroloside (3,5-dihydroxystilben-4′-O-β-D-glucoside) and pinostilbenoside (3-methoxy-5-hydroxystilben-4′-O-β-D-glucoside) with NaOCl and t-BuOCl in the presence of the stable nitroxyl radical TEMPO were studied in various media. It was found that the principal product of pterostilbenoside transformation was its 2,6-dichloroderivative, a part of which was oxidized to form 2,6-dichloropterostilbene glucuronide. Trityl ethers of resveratroloside and pinostilbenoside reacted with the hypochlorites to form mixtures of products.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Prosp. Akad. Lavrent’eva, 9, Novosibirsk, 630090, Russia

    A. D. Rogachev, N. I. Komarova, D. V. Korchagina, V. G. Vasil’ev, N. F. Salakhutdinov & G. A. Tolstikov

  2. Novosibirsk State University, Ul. Pirogova, 2, Novosibirsk, 630090, Russia

    A. V. Pozdeeva

Authors
  1. A. D. Rogachev
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  2. N. I. Komarova
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  3. A. V. Pozdeeva
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  4. D. V. Korchagina
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  5. V. G. Vasil’ev
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  6. N. F. Salakhutdinov
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  7. G. A. Tolstikov
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Correspondence to A. D. Rogachev.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2012, pp. 5–11.

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Rogachev, A.D., Komarova, N.I., Pozdeeva, A.V. et al. Reaction of several resveratrol glycoside derivatives with hypochlorites in various media. Chem Nat Compd 48, 1–7 (2012). https://doi.org/10.1007/s10600-012-0146-z

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  • DOI: https://doi.org/10.1007/s10600-012-0146-z

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