Synthesis of Natural and Sugar-Modified Nucleosides Using the Iodine/Triethylsilane System as N-Glycosidation Promoter
The reagent system based on the combined use of Et<sub>3</sub>SiH/I<sub>2</sub> acts as an efficient <i>N</i>-glycosidation promoter for the synthesis of natural and sugar-modified nucleosides. An analysis of reaction stereoselectivity in the absence of C2-positioned stereodirecting groups revealed high selectivity with six-membered substrates, depending on the nucleophilic character of the nucleobase or based on anomerization reactions. The synthetic utility of the Et<sub>3</sub>SiH/I<sub>2</sub>-mediated <i>N</i>-glycosidation reaction was highlighted by its use in the synthesis of the investigational drug apricitabine.
Authors
- Daniele D’Alonzo
- Annalisa Guaragna (ORCID: https://orcid.org/0000-0001-8684-0622)
- Francesco Zaccaria (ORCID: https://orcid.org/0000-0002-8760-8638)
- Anna Esposito (ORCID: https://orcid.org/0000-0003-0139-8316)
- Maria De Fenza (ORCID: https://orcid.org/0000-0002-2856-5615)
- Martina Cimafonte (ORCID: https://orcid.org/0000-0003-3980-587X)
Institutions
- University of Naples Federico II (IT)
Publication Details
- Journal
- International Journal of Molecular Sciences
- Published
- 2024-08-20
- DOI
- https://doi.org/10.3390/ijms25169030
- Primary Topic
- Biochemical and Molecular Research
- Type
- article
- Field-Weighted Citation Impact
- 0.00