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    朱晨江, 李军廷, 石焱, 唐燕辉, 陈国荣. 维生素E麦芽糖碳糖苷类似物的合成[J]. 华东理工大学学报(自然科学版), 2009, (1): 85-90.
    引用本文: 朱晨江, 李军廷, 石焱, 唐燕辉, 陈国荣. 维生素E麦芽糖碳糖苷类似物的合成[J]. 华东理工大学学报(自然科学版), 2009, (1): 85-90.
    Synthesis of C-D-Glycopyranosylmaltoside Derivatives of Vitamin E[J]. Journal of East China University of Science and Technology, 2009, (1): 85-90.
    Citation: Synthesis of C-D-Glycopyranosylmaltoside Derivatives of Vitamin E[J]. Journal of East China University of Science and Technology, 2009, (1): 85-90.

    维生素E麦芽糖碳糖苷类似物的合成

    Synthesis of C-D-Glycopyranosylmaltoside Derivatives of Vitamin E

    • 摘要: 1,2,3,6,2′,3′,4′,6′-八-O-乙酰基-β-麦芽糖与二甲基对甲氧基苯通过Friedel-Craft烷基化反应形成稳定的碳糖苷,经硝酸铈氨(CAN)氧化、低亚硫酸钠还原、无水氯化锌催化分子内醚化反应,合成了两类结构稳定且保留抗氧活性基团的新型VE麦芽糖碳糖苷类似物——包括ε-VE类的8-(2′, 3′, 6′, 2″, 3″, 4″, 6″-七-O-乙酰基-β-麦芽糖基)-6-羟基-2, 2, 5, 7-四甲基苯并二氢吡喃(10)和8-(2′, 3′, 6′, 2″, 3″, 4″, 6″-

       

      Abstract: With stable structures and antioxidant groups, two series of novel C-D-glycopyranosylmaltoside derivatives of Vitamin E, including ε-VE: 8-(2′, 3′, 6′, 2″, 3″, 4″, 6″-hepta-O-acetyl-β-maltosyl)-6-hydroxy-2, 2, 5, 7-tetramethylchroman(10), 8-(2′, 3′, 6′, 2″, 3″, 4″, 6″-hepta-O-acetyl-β-maltosyl)-ε-VE (11), and γ-VE: 5-(2′, 3′, 6′, 2″, 3″, 4″, 6″-hepta-O-acetyl-β-maltosyl)-6-hydroxy-2, 2, 7, 8-tetramethylchroman(12), 5-(2′, 3′, 6′, 2″, 3″, 4″, 6″-hepta-O-acetyl-β-maltosyl)-γ-VE(13) and 5-(β-maltosyl)-6hydroxy2, 2, 7, 8-tetramethylchroman (14) were synthesized from ceric ammonium nitrate (CAN) oxidation, sodium hydrosulfite reduction and intermolecular etherification catalyzed by anhydrous zinc chloride of stabilized C-glycosides which were prepared by Friedel-Craft reaction between 1, 2, 3, 6, 2′, 3′, 4′, 6′-octa-O-acetyl-β-maltose and bis-methyl-1, 4-dimethyoxybenzene. The structures of synthesized intermediates and products were identified by 1HNMR and MS spectra.

       

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