C??D??Glucopyranosyl Derivatives of Tocopherols–Synthesis and Evaluation as Amphiphilic Antioxidants

…, GR Chen, O Dangles, B Fenet, JP Praly

Index: He, Li; Galland, Stephanie; Dufour, Claire; Chen, Guo-Rong; Dangles, Olivier; Fenet, Bernard; Praly, Jean-Pierre European Journal of Organic Chemistry, 2008 , # 11 p. 1869 - 1883

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Citation Number: 5

Abstract

Abstract Treatment of dimethylhydroquinone dimethyl ethers (ortho and meta isomers) with glycopyranose pentaacetates (D-gluco, D-galacto) in the presence of SnCl 4 and F 3 CCO 2 Ag selectively afforded the corresponding C-β-D-glycosyl derivatives by aromatic electrophilic substitution. Oxidation of the dimethoxybenzene moiety with ceric ammonium nitrate delivered C-β-D-glycosyl-dimethylbenzoquinones, which were reduced with Na 2 S ...