Carbohydrate Experiments in the Organic Laboratory: A Robust Synthesis and Modification of Thioglycosides
Carbohydrate Experiments in the Organic Laboratory: A Robust Synthesis and Modification of Thioglycosides
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DOI：
10.1021/acs.jchemed.9b00446
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发表时间：
2019-10-01
影响因子：
3
通讯作者：
Demchenko, Alexei, V
中科院分区：
文献类型：
--
作者：
Mannino, Michael P.;Dunteman, Ariel P.;Demchenko, Alexei, V
报道了一种由五乙酸葡萄糖三步合成对甲基2,3,4,6-四- o-苯甲酰-1-硫- β - d -葡萄糖吡喃苷的实验室方案。先前报告的程序已经修改，以适应实验室和学生没有适当的培训或设备需要进行空气敏感化学。教育的重点是在保护群体策略中应用的各种考虑和反应。这个三步合成被设计为在两个5小时的实验阶段完成，但可以扩展到三个阶段。所有化合物的纯化都是通过结晶进行的。利用核磁共振光谱、薄层色谱、熔点、红外光谱、质谱和旋光度对反应产物进行了表征。这项新开发的协议是由在3000级有机化学实验室中单独工作的本科生执行的。学生们在可接受的产率（42-88%）下生成了高纯度的产品。
A robust laboratory protocol for the three-step synthesis of p-tolyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-glucopyranoside from commercial glucose pentaacetate is reported. The previously reported procedures have been modified to accommodate laboratories and students without proper training or equipment needed to conduct air-sensitive chemistry. The educational focus is on the various considerations and reactions that are applied in protecting group strategies. The three-step synthesis is designed to be performed over two 5-hour lab sessions but can be expanded to three sessions. Purification of all compounds is performed through crystallization. The reaction products are characterized using NMR spectroscopy, thin-layer chromatography, melting point, IR spectroscopy, mass spectrometry, and optical rotation. This newly developed protocol was performed by undergraduate students working individually in a 3000-level organic chemistry laboratory. The students generated products with high purity in acceptable yields (42-88%).