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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