Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides
Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides
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DOI：
10.1055/s-0037-1611643
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发表时间：
2019-01
期刊：
影响因子：
2
通讯作者：
Seiji Masui;Y. Manabe;Kohtaro Hirao;A. Shimoyama;T. Fukuyama;I. Ryu;K. Fukase
中科院分区：
文献类型：
--
作者：
Seiji Masui;Y. Manabe;Kohtaro Hirao;A. Shimoyama;T. Fukuyama;I. Ryu;K. Fukase
摘要在流动条件下实现了动力学控制的Fischer糖苷化反应。使用β-羟基取代的磺酸官能化的二氧化硅（HO-SAS）作为酸催化剂。该反应直接将己醛糖转化为动力学上有利的呋喃糖苷，使得能够实际合成呋喃糖苷。在优化反应温度和停留时间后，以较好的产率合成了呋喃葡萄糖苷、呋喃半乳糖苷和呋喃甘露糖苷。
Abstract Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.