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

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, N 3, and F), while the corresponding 2′...

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Bibliographic Details
Published in:Tetrahedron 2012-01, Vol.68 (4), p.1253-1261
Main Authors: Choi, Won Jun, Ko, Yun Jung, Chandra, Girish, Lee, Hyuk Woo, Kim, Hea Ok, Koh, Hyo Jung, Moon, Hyung Ryong, Jung, Young Hoon, Jeong, Lak Shin
Format: Article
Language:English
Subjects:
Anti-HCV activity
Assaying
Carbocyclic nucleosides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Conversion
Cyclic sulfate
Exact sciences and technology
Fluorometers
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Iodides
Ketones
Nucleophiles
Nucleosides
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
Stereoselective epoxidation
Sulfur ylide
Tetrahedrons
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Summary: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, N 3, 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.11.052