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Deoxygenative olefination reaction as the key step in the syntheses of deoxy and iminosugars
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Deoxygenative olefination reaction as the key step in the syntheses of deoxy and iminosugars

Yung Chang Hsu and Jih Ru Hwu
Chemistry - A European Journal, Vol.18(25), pp.7686-7690
18/06/2012

Abstract

Benzyne Carbohydrates Iminosugars Olefination Total synthesis
Just a spoonful of sugar! A new synthetic strategy involving the use of a deoxygenative olefination reaction as the key step was developed for the preparation of deoxy and iminosugars in their optically active form (see scheme). This strategy has been proven successful by the use of a pentose, hexose, heptose, and disaccharide as the starting materials. Furthermore, it was applied in a formal total synthesis of iminosugar (-)-1-deoxy-l- fuconojirimycin, which can inhibit a-l-fucosidase. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.

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