相转移催化法合成α-紫罗兰醇-β-D-葡萄糖苷工艺研究  

Study on synthesis of α-ionol-β-D-glucoside by phrase transfer catalytic method

作　　者：张改红[1] 刘宇[1] 李雪龙[1] 潘鹏[1] 柯宁[1] 白冰[1] 毛多斌[1] ZHANG Gai-hong;LIU Yu;LI Xue-long;PAN Peng;KE Ning;BAI Bing;MAO Duo-bin(College of Food and Bioengineering,Zhengzhou University of Light Industry,Zhengzhou 450001,China)

机构地区：[1]郑州轻工业学院食品与生物工程学院,河南郑州450001

出　　处：《轻工学报》2017年第4期43-48,共6页Journal of Light Industry

基　　金：国家级大学生创新创业训练计划项目(201510462046);河南省教育厅科学技术重点研究项目(14A550017)

摘　　要：以α-紫罗兰酮为原料,经选择性还原得到α-紫罗兰醇,α-紫罗兰醇与溴代四乙酰葡萄糖在相转移催化剂四丁基溴化铵(TBAB)作用下进行反应得到α-紫罗兰醇-2,3,4,6-四-O-乙酰基-β-D-葡萄糖苷,最后脱去乙酰基得到目标糖苷.糖苷化反应适宜的反应条件为:以TBAB为相转移催化剂,用量为10%(摩尔百分比);以氯仿-水为反应溶剂;n(溴代四乙酰葡萄糖)∶n(α-紫罗兰醇)=1.6∶1;反应温度60℃;反应时间8 h.该条件下糖苷化反应产率为30%.目标化合物经FT-IR,1H NMR,ESI-MS确证为β-构型.α-ionol was synthesized from α-ionone via the selective reduction. α-ionol-β-D-glucoside was synthesized from α-ionol via the reaction with tetra-O-α-acetyl-D-glucopyranosyl bromide under the phase transfer catalyst to give the corresponding α-ionol-2,3,4,6-tetra-O-acetyl-β-D-glucoside,followed by deacetylation. The appropriate conditions for this glucosidation reaction were as follows： 10% tetrabutyl ammonium bromide was added to catalyze a reaction between Br-glucose-tetraacetateand α-ionol at a ratio of 1. 6 ∶1 in CHCl_3-H_2O allowed to proceed for 8 h at 60 ℃. The yield rate of glycosylation reaction was 30%. The target products were characterized β-configuration by FT-IR,1H NMR and ESI-MS.

关 键 词：相转移催化法 α-紫罗兰醇-β-D-葡萄糖苷 糖苷化 

分 类 号：O621.3[理学—有机化学] TS411[理学—化学]