title: Practical silyl protection of ribonucleosides.
abstract: Herein we report the site-selective silylation of the ribonucelosides. The method enables a simple and efficient procedure for accessing suitably protected monomers for automated RNA synthesis. Switching to the opposite enantiomer of the catalyst allows for the selective silylation of the 3'-hydroxyl, which could be used in the synthesis of unnatural RNA or for the analoging of ribonucelosides. Lastly, the procedure was extended to ribavirin a potent antiviral therapeutic.
authors.affiliation: Institute of Chemical Research of Catalonia , Av. Paisos Catalans 16, 43007 Tarragona, Spain, and Boston College , 2609 Beacon Street, Chestnut Hill, Massachusetts 02467-3860, United States.
authors.forename: Thomas P
authors.initials: TP
authors.lastname: Blaisdell
authors.forename: Sunggi
authors.initials: S
authors.lastname: Lee
authors.forename: Pinar
authors.initials: P
authors.lastname: Kasaplar
authors.forename: Xixi
authors.initials: X
authors.lastname: Sun
authors.forename: Kian L
authors.initials: KL
authors.lastname: Tan
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D017665:Hydroxyl Radical / Q000737:chemistry; D015394:Molecular Structure; D012313:RNA / Q000138:chemical synthesis; D012254:Ribavirin / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000998:Antiviral Agents; D012263:Ribonucleosides; D012821:Silanes; D017665:Hydroxyl Radical; D012254:Ribavirin; D012313:RNA