Synthesis of 1′-(4′-Thio-β-d-Ribofuranosyl) Uracil

Mieke Guinan, Gavin J. Miller, Dylan Lynch, Mark Smith

Research output: Chapter in Book/Report/Conference proceedingChapter (peer-reviewed)peer-review


4'-Thionucleosides, where the furanose ring oxygen is replaced with sulfur, have attracted significant interest due to their biological activity and metabolic stability. In recent years, a growing number of reports have detailed the chemical synthesis and evaluation of 4'-thio nucleoside analogs, alongside methodologies for the provision of thiosugar-containing scaffolds. The original report for synthesizing was made by Imbach and coworkers in their synthesis of 4'-thio-ß-d-oligoribonucleotides and utilized as the starting material, recording a 38% yield for the two-step process. NMR analysis confirmed the correct structure notably with the presence of signals for the alkene in the nucleobase with vicinal coupling to each other.
Original languageEnglish
Title of host publicationCarbohydrate Chemistry
Subtitle of host publicationProven Synthetic Methods
EditorsPaul Kosma, Tanja Wrodnigg, Arnold Stütz
Place of PublicationBoca Raton
PublisherCRC Press
Number of pages6
ISBN (Electronic)9781351256087
ISBN (Print)9780815367888 (hbk), 9780367561734 (pbk)
Publication statusPublished - 2021


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