Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation
Tinghua Wang
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, 63121 St. Louis, Missouri, USA
Search for more papers by this authorYashapal Singh
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, 63121 St. Louis, Missouri, USA
Search for more papers by this authorKeith J. Stine
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, 63121 St. Louis, Missouri, USA
Search for more papers by this authorCorresponding Author
Alexei V. Demchenko
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, 63121 St. Louis, Missouri, USA
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA
E-mail: [email protected]
www: http://www.umsl.edu/chemistry/Faculty/demchenko.html
Search for more papers by this authorTinghua Wang
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, 63121 St. Louis, Missouri, USA
Search for more papers by this authorYashapal Singh
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, 63121 St. Louis, Missouri, USA
Search for more papers by this authorKeith J. Stine
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, 63121 St. Louis, Missouri, USA
Search for more papers by this authorCorresponding Author
Alexei V. Demchenko
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, 63121 St. Louis, Missouri, USA
Department of Chemistry and Biochemistry, University of Missouri – St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA
E-mail: [email protected]
www: http://www.umsl.edu/chemistry/Faculty/demchenko.html
Search for more papers by this authorGraphical Abstract
TOC: The first attempt to use glycosyl nitrates as glycosyl donors for O-glycosylation is presented. Lanthanide ions with higher charge-to-size ratios showed good affinity to bind the nitrate leaving group. High reaction yields were achieved with per-benzylated and per-benzoylated donors of the d-glucose and d-galactose series with both primary and secondary glycosyl acceptors in various solvents.
Abstract
Glycosyl nitrates are important synthetic intermediates in the synthesis of 2-amino sugars, 1,2-orthoesters or, more recently, 2-OH glucose. However, glycosyl nitrates have never been glycosidated. Presented herein is our first attempt to use glycosyl nitrates as glycosyl donors for O-glycosylation. Lanthanide triflates showed good affinity to activate the nitrate leaving group.
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