Rhys Batchelor, Peter T. Northcote, and Joanne E. Harvey
School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington, New Zealand
Emma M. Dangerfield and Bridget L. Stocker
The Malaghan Institute Medical Research, Wellington, New Zealand
Carbohydrates, in the form of glycoconjugates, have recently been shown to control a wide range of cellular processes. Accordingly, students interested in the study of organic chemistry and biomedical sciences should be exposed to carbohydrate chemistry. To this end, we have developed a sequence of experiments that leads the student from the derivatization of naturally occurring D-glucose through to the formation of simple alkyl and aryl glycosides, and in doing so this experiment provides a comprehensive overview of the fundamentals of glycoside synthesis. These experiments focus on the control of stereochemistry at the anomeric center and NMR spectroscopy for the structural elucidation of products.
Supplement
Handouts from the student laboratory manual; Notes for the teaching assistants; NMR spectra (1D and 2D)
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