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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
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JoVE Journal Chemistry
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

DOI:
10.3791/57897-v

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08:46 min

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July 26, 2018

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, , ,
1Faculty of Pharmaceutical Sciences,Tokyo University of Science, 2Imaging Frontier Center,Tokyo University of Science

Chapters

  • 00:04Title
  • 00:51Procedure for O-Glycosylation Reactions
  • 05:59NMR Studies of Cyclic Boronic Ester
  • 07:28Results: O-Glycosylations of Nucleosides Utilizing Temporary Protection of 2 ,3 -Diol by Boronic Ester
  • 08:08Conclusion

Summary

Automatic Translation

Automatic Translation

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.

Tags

Keywords: Regioselective O-glycosylationNucleosideBoronic EsterDisaccharide NucleosideTemporary Diol ProtectionDrug DiscoveryGlycosylationUnprotected NucleosideReaction OptimizationSynthesis

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