ERIC Number: EJ1231341
Record Type: Journal
Publication Date: 2019-Oct
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Carbohydrate Experiments in the Organic Laboratory: A Robust Synthesis and Modification of Thioglycosides
Mannino, Michael P.; Dunteman, Ariel P.; Demchenko, Alexei V.
Journal of Chemical Education, v96 n10 p2322-2325 Oct 2019
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%).
Descriptors: Organic Chemistry, Science Laboratories, Laboratory Experiments, Laboratory Procedures, Spectroscopy, College Science, Science Instruction, Undergraduate Students, Chemistry
Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A