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.
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