一种用于检测微生物的4-甲基伞形酮基糖苷α/β-立体选择性合成的改进赫尔弗里希方法。
An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms.
作者信息
Wei Xianhu, Ma Yanxia, Wu Qingping, Zhang Jumei, Cai Zhihe, Lu Mianfei
机构信息
Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, China.
State Key Laboratory of Applied Microbiology Southern China, Guangdong Institute of Microbiology, Guangzhou 510070, China.
出版信息
Molecules. 2015 Dec 4;20(12):21681-99. doi: 10.3390/molecules201219789.
An improved Helferich method is presented. It involves the glycosylation of 4-methyl-umbelliferone with glycosyl acetates in the presence of boron trifluoride etherate combined with triethylamine, pyridine, or 4-dimethylaminopyridine under mild conditions, followed by deprotection to give fluorogenic 4-methylumbelliferyl glycoside substrates. Due to the use of base, the glycosylation reaction proceeds more easily, is uncommonly α- or β-stereoselective, and affords the corresponding products in moderate to excellent yields (51%-94%) under appropriate conditions.
提出了一种改进的赫尔弗里希方法。该方法涉及在三氟化硼乙醚络合物与三乙胺、吡啶或4-二甲氨基吡啶存在下，于温和条件下将4-甲基伞形酮与糖基乙酸酯进行糖基化反应，随后进行脱保护反应以得到荧光性4-甲基伞形酮基糖苷底物。由于使用了碱，糖基化反应更容易进行，具有罕见的α-或β-立体选择性，并且在适当条件下能以中等至优异的产率（51%-94%）得到相应产物。
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