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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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Correspondence to A. D. Rogachev.

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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).

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