Stereoselective Synthesis of α-Digitoxosides and α-Boivinosides via Chelation-Controlled Anomeric O-Alkylation |
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| Authors: | Danyang Zhu Surya Adhikari Kedar N Baryal Belal N Abdullah |
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| Institution: | Department of Chemistry and School of Green Chemistry and Engineering, University of Toledo, Toledo, Ohio 43606 |
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| Abstract: | A chelation-controlled anomeric O-alkylation has been developed for the stereoselective synthesis of α-digitoxosides and α-boivinosides bearing a C3-free hydroxyl group. Due to chelation via sodium ion, the anomeric alkoxides are locked in the axial configuration, which leads to the selective production of α-glycosides. |
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| Keywords: | 2-Deoxy sugars Anomeric O-alkylation Glycosylation Chelation control Oligosaccharide synthesis |
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