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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-εVE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″-七-O-乙酰基-β-麦芽糖基)--εVE(11),-γVE类的5-(2,′3′,6,′2,″3,″4,″6″-七-O-乙酰基-β-麦芽糖基)-6-羟基-2,2,7,8-四甲基苯并二氢吡喃(12)、5-(2′,3,′6,′2,″3,″4,″6″-七-O-乙酰基-β-麦芽糖基)--γVE(13)以及5-(β-麦芽糖基)-6-羟基-2,2,7,8-四甲基苯并二氢吡喃(14)。反应中间体及目标产物由1H-NMR和MS表征。
【Abstract】 With stable structures and antioxidant groups,two series of novel C-D-glycopyranosylmaltoside derivatives of Vitamin E,including ε-V_E: 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-V_E(11),and γV_E: 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-V_E(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.
- 【文献出处】 华东理工大学学报(自然科学版) ,Journal of East China University of Science and Technology(Natural Science Edition) , 编辑部邮箱 ,2009年01期
- 【分类号】O621.25
- 【下载频次】166