Extension of the Ring Oxygen Helicity Rule to Phenyl and p-Nitrophenyl Glycopyranosides

The Cotton effect below 200 nm was first studied in aromatic glycopyranosides with our new technique of optical rotatory dispersion (ORD). The phenyl and p-nitrophenyl α- and β-d-glycopyranosides showed a strong Cotton effect at around 180 nm which practically governed the optical rotations in the visible wavelength region. The rotational strength and sign of this Cotton effect were shown to reflect the anomeric configurations and conformations, which led to an extension of the ring oxygen helicity rule for alkyl and alkyl 1-thioglycosides to aromatic glycopyranosides.