13C-NMR glycosylation effects in (1→3)-linked furanosyl-pyranosides

•Six (1→3)-linked furanosyl-pyranosides have been synthesized.•13C NMR glycosylation effects have been measured for these compounds.•Several conformers have been revealed during theoretical conformational analysis.•These conformers are used to explain the observed glycosylation effects.

Synthesis, theoretical conformational analysis (molecular mechanics and DFT calculations) and NMR spectral data including the 13C-NMR glycosylation effects for six pairs of isomeric furanosyl-(1→3)-pyranosides with different anomeric and absolute configurations of furanosyl units as well as configurations of C2 and C4 in the pyranoside units are described. The determined 13C-NMR glycosylation effects were shown to correlate with the pattern of intramolecular interactions around the inter-unit bonds.

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