regioselective-o-glycosylation-nucleosides-via-temporary-2-3-diol

Regioselective <em>O</em>-Glycosylation of Nucleosides <em>via</em> the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Disaccharide nucleosides, which consist of disaccharide and nucleobase moieties, have been known as a valuable group of natural products having ...

Tokyo University of Science

Tokyo University of science

Disaccharide nucleosides are an important class of natural compounds that have a variety of biological activities. In this study, we report on the synthesis of disaccharide nucleosides utilizing the temporary protection of the 2',3'--diol of ribonucleosides, such as adenosine, guanosine, uridine, 5-metyluridine, 5-fluorouridine and cytidine, by a boronic ester. The temporary protection of the above ribonucleosides permits the regioselective -glycosylation of the 5'-hydroxyl group with thioglycosides using a -toluenesulfenyl chloride (-TolSCl)/silver triflate (AgOTf) promoter system to afford the corresponding disaccharide nucleosides in fairly good chemical yields. The formation of a boronic ester prepared from uridine and 4-(trifluoromethyl)phenylboronic acid was examined by ¹H, B and F NMR spectroscopy.

Hidehisa Someya

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