Beilstein J. Org. Chem.2019,15, 2990–2999, doi:10.3762/bjoc.15.295
order to access glycans in a pure form. In line with this, various C-5-substituted 2,7-anhydrosialicacid derivatives bearing both electron-donating and -withdrawing protecting groups were synthesized and subjected to different Lewis acid-catalyzed solvent-free ring-opening reactions at room temperature
thiosialoside and halide donors.
Keywords: acetolysis; acetolysis products; 2,7-anhydrosialicacid; SnCl4; Introduction
Sialic acids are the most prevalent monosaccharides that are found at the nonreducing ends of glycans, and they are involved in many biologically important ligand–receptor interactions [1
the hydroxymethyl group in 10 to furnish 11 in 82% yield.
After having obtained the 2,7-anhydrosialicacid derivatives 5–11, they were subjected to various Lewis acid-catalyzed ring-opening reactions. In line with this, Sc(OTf)3-, copper(II) triflate-, and SnCl4-catalyzed acetolysis of diacetylamino
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Graphical Abstract
Figure 1:
Representative structures of bacterial glycans containing sialic acid.