Carbohydrate Experiments in the Organic Laboratory: A Robust Synthesis and Modification of Thioglycosides
| Autor: | Michael P. Mannino, Ariel P. Dunteman, Alexei V. Demchenko |
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| Rok vydání: | 2019 |
| Předmět: |
Protocol (science)
Science instruction Materials science 010405 organic chemistry Glucose pentaacetate 05 social sciences 050301 education Infrared spectroscopy General Chemistry Nuclear magnetic resonance spectroscopy 01 natural sciences 0104 chemical sciences Education Organic chemistry Protecting group 0503 education |
| Zdroj: | Journal of Chemical Education. 96:2322-2325 |
| ISSN: | 1938-1328 0021-9584 |
| DOI: | 10.1021/acs.jchemed.9b00446 |
| Popis: | 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%). |
| Databáze: | OpenAIRE |
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