Novel epimerization of aromatic C-nucleosides with electron-withdrawing substituents with trifluoroacetic acid-benzenesulfonic acid using mild conditions |
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Authors: | Yu Lin JiangJames T Stivers |
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Affiliation: | Department of Pharmacology and Molecular Sciences, Johns Hopkins University School of Medicine, 725 North Wolfe Street, Baltimore, MD 21205-2185, USA |
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Abstract: | Trifluoroacetic acid and benzenesulfonic acid in dichloromethane at ambient temperature have been found to be efficient co-catalysts for the epimerization of C-nucleosides with electron-withdrawing substituents. This approach provides a convenient route to the β anomer of the nucleosides with high yields in the range 54-78%. Synthesis of the 3′-phosphoramidite of 2,4-difluorophenyl C-nucleoside suitable for solid-phase DNA synthesis is described. |
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Keywords: | epimerization C-nucleosides trifluoroacetic acid benzenesulfonic acid dichloromethane |
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