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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Glycochemical Applications of Diels-Alder Reaction

Author(s): Sylvain Laclef, Sylvestre Toumieux and José Kovensky

Volume 20, Issue 22, 2016

Page: [2379 - 2392] Pages: 14

DOI: 10.2174/1385272820666160502163125

Price: $65


Carbohydrates and their analogs are key molecules with a wide range of biological activities. These bioactive compounds are usually synthesized through derivatization of naturally occurring carbohydrates. Nevertheless, this strategy suffers from a limited range of naturally available monosaccharide building blocks and the necessity of laborious steps of protection and deprotection. Consequently new methods began to emerge and Diels-Alder reaction appeared to be a method of choice for their de novo production. The synthesis of carbohydrates and their analogs by means of cycloaddition reactions will be reviewed here. Moreover the potentiality of the use of monosaccharides to induce chirality in Diels-Alder reaction will be presented. Efficient methods for the synthesis of di- and trisaccharides using the developments shown previously will be also introduced.

Keywords: Asymmetric synthesis, aza-sugars, carbohydrates, chiral auxiliary, diels-Alder, disaccharides, hetero-Diels-Alder reaction, thiosugars.

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