Stereoselective synthesis and anti-HCV activity of conformationally restricted 2′-C-substituted carbanucleosides

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Abstract

Conformationally restricted 2′-C-azido-, hydroxy- and fluoromethyl-carbanucleosides 4b-f were efficiently synthesized via the stereoselective conversion of ketone 7 to epoxide 14, followed by the stereoselective opening of the epoxide with nucleophiles (OAc, N3, and F), while the corresponding 2′-C-methyl-carbanucleoside 4a was synthesized via the stereoselective Grignard reaction of ketone 7 with methylmagnesium iodide as a key step. All the final nucleosides 4a-f were assayed for anti-HCV activity, but showed neither significant anti-HCV activity nor cytotoxicity in a cell-based replicon assay. © 2011 Elsevier Ltd. All rights reserved.

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Choi, W. J., Ko, Y. J., Chandra, G., Lee, H. W., Kim, H. O., Koh, H. J., … Jeong, L. S. (2012). Stereoselective synthesis and anti-HCV activity of conformationally restricted 2′-C-substituted carbanucleosides. Tetrahedron, 68(4), 1253–1261. https://doi.org/10.1016/j.tet.2011.11.052

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