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Synthesis of 4-Methylumbellifer-7-yl-alpha-D-Mannopyranoside: An Introduction to Modern Glycosylation Reactions
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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.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
CarbohydratesCiting Articles
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
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Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside
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Alexei V. Demchenko , Papapida Pornsuriyasak and Cristina De MeoJournal of Chemical Education2006 83 (5), 782A 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 ...
One-Pot Synthesis of 7-Hydroxy-3-carboxycoumarin in Water
Francesco Fringuelli , Oriana Piermatti and Ferdinando PizzoJournal of Chemical Education2004 81 (6), 874One-Pot Synthesis of 7-Hydroxy-3-carboxycoumarin in Water
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- Received: August 03, 2009
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