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In the Laboratory
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Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside
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Alexei V. Demchenko, Papapida Pornsuriyasak, and Cristina De Meo
Department of Chemistry and Biochemistry, University of Missouri–St. Louis, St. Louis, MO 63121
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May 2006
Vol. 83 No. 5
p. 782
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| Abstract |
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A laboratory procedure for the synthesis of methyl 4,6-O-benzylidene-α-D-glucopyranoside is described. This compound is obtained in one synthetic step from commercially available methyl α-D-glucopyranoside. Purification of the target compound is achieved by precipitation from organic solvents. The experiment has given our undergraduate students an exposure to practical synthetic carbohydrate chemistry. In addition, the experiment provides an opportunity to synthesize a cyclic acetal; stereoselectively introduce a chirality center; learn extraction, evaporation, precipitation, optical rotation, melting point measurement, thin-layer chromatography, IR-spectroscopy, mass spectrometry, and various NMR techniques. The extended experiment for the advanced organic laboratory as a part of a multistep synthesis or identification of unknowns has been also developed.
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| Supplement |
Notes for the student, suggestions for the instructor, experimental procedure, suggested application in a multistep synthesis, and sample characterization data are available.
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 Contents |
Folder JCE2006p0782W containing JCE2006p0782W.doc (Microsoft Word) and JCE2006p0782W.ppt (Microsoft PowerPoint)
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| More Information |
Citation |
Demchenko, Alexei V.; Pornsuriyasak, Papapida; De Meo, Cristina. J. Chem. Educ. 2006 83 782.
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Keywords |
Carbohydrates; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; Medicinal Chemistry; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Synthesis; Thin Layer Chromatography; Upper-Division Undergraduate
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History |
Created:
Last Updated: |
3/16/2006
3/31/2006
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