Resumen de Carbohydrate Experiments in the Organic Laboratory: A Robust Synthesis and Modification of Thioglycosides
Michael P. Mannino, Ariel P. Dunteman, Alexei V. Demchenko
A robust laboratory protocol for the three-step synthesis of p-tolyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-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%).
