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。
With stable structures and antioxidant groups, two series of novel C-D-glycopyranosylmal- toside 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-(2r, 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.