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Monosaccharides as Potential Chiral Probes for the Determination of the Absolute Configuration of Secondary Alcohols

Laskowski, Tomasz, Szwarc, Katarzyna, Szczeblewski, Paweł, Sowiński, Paweł, Borowski, Edward, Pawlak, Jan
Journal of natural products 2016 v.79 no.11 pp. 2797-2804
alcohols, carbon, glycosides, glycosylation, monosaccharides, nuclear magnetic resonance spectroscopy, protons, stereochemistry
Herein, a new method for the elucidation of the absolute configuration of chiral secondary alcohols is proposed. This method is an alternative for a widely used approach reported by Mosher and Dale and similar methods that are based on the ¹H NMR shift (δ) changes of protons that are attached to the substituents of the oxymethine carbon atom. The presented method is not based on tracking the chemical shift changes and utilizes stereochemically defined monosaccharides as chiral probes. A secondary alcohol is glycosylated, and the resulting glycoside is subjected to NMR studies. The observation of dipolar couplings between the protons of the monosaccharide moiety and the protons of the secondary alcohol moiety via the NOESY/ROESY spectra enables the determination of the absolute configuration of the oxymethine carbon atom.