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Assignment of the 1H, 19F, and 13C NMR spectra of 2-deoxy-2-fluoro-d-ribose and characterisation of the isomeric equilibrium

✍ Scribed by Paul N. Sanderson; Brian C. Sweatman; R.Duncan Farrant; John C. Lindon

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 455 KB
Volume: 284
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(96)00020-1

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✦ Synopsis

The assignment of the ~H, 19F, and 13C NMR chemical shifts and coupling constants of 2-deoxy-2-fluoro-o-ribose, an important intermediate in the synthesis of antiviral nucleoside drugs, is reported and the NMR spectra are used to determine the proportions of the pyranose and furanose forms together with the anomeric ratios in acetone-d 6 solution. The/3-pyranose isomer is shown to exist at equilibrium with both 4C~ and ~C 4 conformations in approximately equal proportions in fast exchange. The a-pyranose isomer at equilibrium is predominantly in the 4Cj i form but the C 4 conformer is also present in solution, the two forms being in intermediate 19 • • 1 13 •

exchange on the F NMR tlmescale but m fast exchange on the H and C NMR umescales. For both the pyranose and furanose forms, the /3-anomer predominates. The results are similar to those for o-ribose.

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