Synthesis of 4-methylumbellifer-7-yl-alpha-D-mannopyranoside: an introduction to modern glycosylation reactions

Fourth-year organic chemistry students can learn about modern glycosylation reactions by carrying out the 4-step synthesis of 4-methylumbellifer-7-yl-alpha-D-mannopyranoside. Students find the lab exciting because they are introduced to the interpretation of 2D-NMR spectra and because reaction times are very short. The target is mannosylated coumarin and it was prepared, apparently for the first time, using the trichloroacetimidate method in the development of this exercise. Glycochemistry is increasingly of interest, being attractive for biological, medical, and pharmaceutical applications. Two 4-hour labs are needed.