Protecting Group Control of Hydroxyketone-Hemiketal Tautomeric Equilibrium Enables the Stereoselective Synthesis of a 1 ' -Azido C -Nucleoside.

Autor: Panda S; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States., Orimoloye MO; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States., Poudel TN; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States., De Jonghe S; Department of Microbiology, Immunology & Transplantation, Faculty of Medicine, University of Leuven, (KU Leuven), Leuven 3000, Belgium., Jochmans D; Department of Microbiology, Immunology & Transplantation, Faculty of Medicine, University of Leuven, (KU Leuven), Leuven 3000, Belgium., Neyts J; Department of Microbiology, Immunology & Transplantation, Faculty of Medicine, University of Leuven, (KU Leuven), Leuven 3000, Belgium., Aldrich CC; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Dec 06; Vol. 89 (23), pp. 17389-17399. Date of Electronic Publication: 2024 Nov 19.
DOI: 10.1021/acs.joc.4c01981
Abstrakt: The synthesis of 1 ' -azido C -nucleosides is described to expand the set of azide-functionalized nucleosides for bioorthogonal applications and as potential antiviral drugs. Lewis acid-promoted azidation of a nucleoside hemiketal resulted in the formation of a tetrazole through a Schmidt reaction manifold. Conformational control to prevent ring-chain tautomerism enabled efficient 1 ' -azidation with complete β-diastereoselectivity. The unique reactivity and further derivation of the 1 ' -azido C -nucleosides are also reported.
Databáze: MEDLINE
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