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)-6hydroxy2, 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 1HNMR and MS spectra.