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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

J. Chem. Educ., 2006, 83 (5), p 782

DOI: 10.1021/ed083p782

Publication Date (Web): May 1, 2006

Section:

History, Education, and Documentation

Abstract

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Carbohydrates

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