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Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides

Sujit ManmodeDepartment of Chemistry and Biotechnology, Graduate School of Engineering Tottori University 4-101 Koyamachominami Tottori city 680-8552 Tottori Japan E-maiShichidai TanabeDepartment of Chemistry and Biotechnology, Graduate School of Engineering Tottori University 4-101 Koyamachominami Tottori city 680-8552 Tottori Japan E-maiTakashi YamamotoDepartment of Chemistry and Biotechnology, Graduate School of Engineering Tottori University 4-101 Koyamachominami Tottori city 680-8552 Tottori Japan E-maiNorihiko SasakiDepartment of Chemistry and Biotechnology, Graduate School of Engineering Tottori University 4-101 Koyamachominami Tottori city 680-8552 Tottori Japan E-maiToshiki NokamiCenter for Research on Green Sustainable Chemistry, Faculty of Engineering Tottori University 4-101 Koyamachominami Tottori city 680-8552 Tottori JapanToshiyuki ItohCenter for Research on Green Sustainable Chemistry, Faculty of Engineering Tottori University 4-101 Koyamachominami Tottori city 680-8552 Tottori Japan
2019en
ABI

Аннотация

Electrochemical glycosylation of a linear oligosaccharide with a protecting-group-free primary hydroxyl group afforded cyclic oligo-saccharides, up to hexasaccharides, in high yields. Precursors of the cyclic oligosaccharides were prepared by automated electro-chemical assembly-a method for the automated electrochemical solution-phase synthesis of oligosaccharides. We demonstrated that electrochemical glycosylation is useful not only for intermolecular glycosylation but also for intramolecular glycosylation to synthesize cyclic oligosaccharides.

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