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Protecting-Group-Mediated Diastereoselective Synthesis of C4'-Methylated Uridine Analogs and Their Activity against the Human Respiratory Syncytial Virus.
Köllmann, Christoph Sake, Svenja M Jones, Peter G Pietschmann, Thomas Werz, Daniel B
Köllmann, Christoph
Sake, Svenja M
Jones, Peter G
Pietschmann, Thomas
Werz, Daniel B
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2020-02-26
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Abstract
Adjusting the protecting group strategy, from an alkyl ether to a bidentate ketal at the carbohydrate backbone of uridine, facilitates a switchable diastereoselective α- or β-C4'/C5'-spirocyclopropanation. Using these spirocyclopropanated nucleosides as key intermediates, we synthesized a variety of C4'-methylated d-ribose and l-lyxose-configured uridine derivatives by a base-mediated ring-opening of the spirocyclopropanol moiety. Investigations of antiviral activity against the human respiratory syncytial virus were carried out for selected derivatives, showing moderate activity.
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J Org Chem. 2020 Mar 20;85(6):4267-4278. doi: 10.1021/acs.joc.9b03425. Epub 2020 Feb 26.
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en
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1520-6904
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Attribution 4.0 International