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Chemistry

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

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

Article DOI: 10.3791/57897 08:46 min July 26th, 2018
July 26th, 2018

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Summary

Here, we present protocols for the synthesis of disaccharide nucleosides by the regioselective O-glycosylation of ribonucleosides via a temporary protection of their 2',3'-diol moieties utilizing a cyclic boronic ester. This method applies to several unprotected nucleosides such as adenosine, guanosine, cytidine, uridine, 5-methyluridine, and 5-fluorouridine to give corresponding disaccharide nucleosides.

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Regioselective O-Glycosylation Nucleosides Temporary 2',3'-diol Protection Boronic Ester Synthesis Disaccharide Nucleosides Drug Discovery Research Biologically-active Glycosylation Protecting Group Manipulation Visual Demonstration Reaction Conditions Compound Alpha-and Beta-12 Compound Beta-22 Ribonucleoside Adenosine-13 Anhydrous Pyridine Galactosyl Donor Beta-21 Four-Trifluoromethyl Phenylboronic Acid 11C
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