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A study has been made of the  1 H NMR spectra of peracetylated β-glucopyranosides and α-arabinopyranosides obtained by reaction of D- and L-glucoses, and L- and D-arabinoses with either ( R)- or ( S)-2-octanols. The obtained and literature data show that  1 H NMR spectra may be used to determine the absolute configuration of the aglycone moieties of some alicyclic glycosides without the need to synthesize derivatives with chiral reagents, as long as the absolute configuration of their monosaccharide moiety is known or vice versa. Spectra of marine steroid glycosides and their acetates containing glycosylated side chains as alicyclic fragments were also examined. It was shown that analysis of  1 H NMR spectra for the determination of the absolute configuration is more applicable in the cases when glycosides have the same substitution in the D-ring of the aglycone moiety.

natural product communications

Determination of Absolute Stereochemistry of Natural Alicyclic Glycosides by <sup>1</sup>H NMR Spectroscopy without Application of Chiral Reagents – An Indication

Determination of Absolute Stereochemistry of Natural Alicyclic Glycosides by 1H NMR Spectroscopy without Application of Chiral Reagents – An Indication

Determination of Absolute Stereochemistry of Natural Alicyclic Glycosides by ¹H NMR Spectroscopy without Application of Chiral Reagents – An Indication