Comments on conformational studies of monoglycosylated 3-N-alkylcatechols

The variable temperature H-1 NMR spectra of the signals of the C-6 protons of 2-hydroxy-3-methylphenyl beta-D-glucopyranoside (9a) and its 2,3,4,6-tet ra-O-acetyl derivative (2a) had previously been interpreted as indicating t hat there was slow rotation around the C5-C6 bond in 2a and for 9a, that th e fg rotamer was significantly populated while the gt rotamer had a negligi ble population. The data was reanalysed to demonstrate that neither conclus ion was valid.