Resumen de Synthesis of Methyl 2,3,5-Tri-O-benzoyl-α[alpha]-d-arabinofuranoside in the Organic Laboratory
Christopher S. Callam, Todd L. Lowary
We report an organic chemistry laboratory experiment in which methyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside is synthesized. The product is obtained in two steps from commercially available D-arabinose, via Fischer glycosylation and benzoylation. The product is easily purified by crystallization. The primary purpose in implementing this experiment was to give students additional exposure to carbohydrate chemistry. In addition, the experiment provides an opportunity to discuss a number of other topics including kinetic vs thermodynamic control of reactions, mutarotation, the synthesis of esters, recrystallization, the separation of diastereomers, and optical activity. It is also possible to incorporate 2-D NMR spectroscopy into this experiment.
