Stereoselective Synthesis Of 2-Deoxyglycosides Research Articles

Stereoselective Synthesis of 2-Deoxy Glycosides via Iron Catalysis

An Fe-catalyzed 2-deoxy glycosylation method was developed from 3,4-O-carbonate glycals directly at room temperature. This novel approach enabled facile access to alkyl and aryl 2-deoxy glycosides in high yields with exclusive α-stereoselectivity, tolerating various alcohols, phenols, and glycals. The synthetic utility and advantage of this strategy have been demonstrated by the modification of six natural products and the construction of a tetrasaccharide.

Recent progress on the synthesis of 2-deoxy glycosides

2-Deoxy glycosides are widely presented in natural products and clinical reagents. The presence of 2-deoxy glycosides is essential for bioactivities of these compounds. This report provides an overview of the recent advances in the stereoselective synthesis of 2-deoxy glycosides. Particularly, the contents of this review covered the work published since the earlier reviews on this topic by Marzabadi (2000), Lowary (2009), Ding (2012) and Nagorny (2012).

Synthesis of 2-deoxygalactopyranoside derivatives of benzyl alcohols with β-galactosidase from Aspergillus oryzae

The stereoselective synthesis of 2-deoxyglycosides is a challenge. Glycosidases are capable of catalyzing the synthesis of glycosidic linkages by the absolute stereoselectivity of the anomeric center. We report on an efficient stereoselective synthesis of benzyl β-D-2-deoxygalactopyranosides in the reaction of galactal with alcohols catalyzed using β-galactosidase from Aspergillus oryzae.