A Greener Technique for Microwave-Assisted O-Silylation and Silyl Ether Deprotection of Uridine and Other Substrates

Claudia Pasqualini; Federica Poggialini; Chiara Vagaggini; Annalaura Brai; Elena Dreassi

doi:10.3390/chemistry4040112

Chemistry (Dec 2022)

A Greener Technique for Microwave-Assisted O-Silylation and Silyl Ether Deprotection of Uridine and Other Substrates

Claudia Pasqualini,
Federica Poggialini,
Chiara Vagaggini,
Annalaura Brai,
Elena Dreassi

Affiliations

Claudia Pasqualini: Department of Biotechnologies, Chemistry and Pharmacy, University of Siena, Via Aldo Moro 2, I-53100 Siena, Italy
Federica Poggialini: Department of Biotechnologies, Chemistry and Pharmacy, University of Siena, Via Aldo Moro 2, I-53100 Siena, Italy
Chiara Vagaggini: Department of Biotechnologies, Chemistry and Pharmacy, University of Siena, Via Aldo Moro 2, I-53100 Siena, Italy
Annalaura Brai: Department of Biotechnologies, Chemistry and Pharmacy, University of Siena, Via Aldo Moro 2, I-53100 Siena, Italy
Elena Dreassi: Department of Biotechnologies, Chemistry and Pharmacy, University of Siena, Via Aldo Moro 2, I-53100 Siena, Italy

DOI: https://doi.org/10.3390/chemistry4040112
Journal volume & issue: Vol. 4, no. 4
pp. 1714 – 1722

Abstract

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A single clean, good-yielding, environment-friendly microwave-assisted procedure for O-silylation of uridine with tert-butyldimethylsilyl chloride (TBDMSCl), 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU) and potassium nitrate as catalyst under solvent-free conditions is reported. Subsequent silyl ether deprotection is accomplished with a reusable acidic resin via microwave irradiation. Both the silylation and desilylation protocols have been applied to a panel of alcohols of pharmaceutical interest.

Published in Chemistry

ISSN: 2624-8549 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry
Website: https://www.mdpi.com/journal/chemistry

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