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  Home > JCE Print > Journal of Chemical Education > Issues > 2002  > November  >
In the Laboratory
Synthesis of 4-Methylumbellifer-7-yl-α-D-Mannopyranoside: An Introduction to Modern Glycosylation Reactions
Christophe Penverne and Vincent Ferrières
Ecole Nationale Supérieure de Chimie de Rennes, Rennes, France
Cover
November 2002
Vol. 79 No. 11
p. 1353
Abstract
The present work is aimed at introducing fourth-year organic chemistry students to glycochemistry and in particular to the diastereocontrolled synthesis of glycosides. In this context, we have elaborated a hemisynthetic work starting from carbohydrates easily available as natural renewable resources using a modern approach to glycosylation. These reactions led the instructors to highlight how the anomeric center of a glycosyl donor is able to be activated and the role of protecting groups that stabilizes the cationic intermediate and so controls the formation of the new glycosidic linkage. In practice, students are induced to perform successively: (1) a selective deacetylation under mild conditions, (2) the activation of the resulting free hydroxyl that yields an anomeric trichloroacetimidate, (3) the mannosylation of a natural coumarin, and (4) a final deprotection step. This sequence leads to an aromatic glycoside which has potential for biological applications since some inhibition properties have already been established. Consequently, this experiment is suitable to demonstrate the connection between chemistry and life sciences.
Supplement
Instructions for the students and notes for the instructor are available .
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*  Citation
 Penverne, Christophe; Ferrières, Vincent. J. Chem. Educ. 2002 79 1353.
*  Keywords
 Carbohydrates; Laboratory Instruction; Natural Products; Organic Chemistry; Organic Synthesis
*  History
 Created:
Last Updated:		 September 30, 2002
March 16, 2005
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