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Article Dans Une Revue Journal of Organic Chemistry Année : 2023

Obtaining Pure 1H NMR Spectra of Individual Pyranose and Furanose Anomers of Reducing Deoxyfluorinated Sugars

Résumé

Due to tautomeric equilibria, NMR spectra of reducing sugars can be complex with many overlapping resonances. This hampers coupling constant determination, which is required for conformational analysis and configurational assignment of substituents. Given that mixtures of interconverting species are physically inseparable, easy-to-use techniques that enable facile full 1 H NMR characterization of sugars are of interest. Here, we show that individual spectra of both pyranoside and furanoside forms of reducing fluorosugars can be obtained using 1D FESTA. We discuss the unique opportunities offered by FESTA over standard sel-TOCSY and show how it allows a more complete characterization. We illustrate the power of FESTA by presenting the first full NMR characterization of many fluorosugars, including of the important fluorosugar 2-deoxy-2fluoroglucose. We discuss in detail all practical considerations for setting up FESTA experiments for fluorosugars, which can be extended to any mixture of fluorine-containing species interconverting slowly on the NMR frequency−time scale.
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Origine : Publication financée par une institution
Licence : CC BY - Paternité

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hal-04304362 , version 1 (24-11-2023)

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Gabija Poškaitė, David E Wheatley, Neil Wells, Bruno Linclau, Davy Sinnaeve. Obtaining Pure 1H NMR Spectra of Individual Pyranose and Furanose Anomers of Reducing Deoxyfluorinated Sugars. Journal of Organic Chemistry, 2023, 88 (19), pp.13908 - 13925. ⟨10.1021/acs.joc.3c01503⟩. ⟨hal-04304362⟩
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