APPLICATION OF LANTHANIDE SHIFT-REAGENTS TO H-1-NMR AND C-13-NMR SPECTRA OF SOME CARBOHYDRATE-DERIVATIVES

N.m.r line-shifts (1H and 13C) induced by Eu(fod)3 in the spectra of methyl 4,6-O-benzylidene-3-O-methyl-β-d-glucopyranoside (1), methyl 4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl)-α-d-mannopyranoside (2), and methyl 4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-α-d-glucopyranoside (3) have been measured. The shift data allow a complete assignment of the 1H- and 13C-n.m.r. spectra of 1. However, it was necessary to consider the spectra of the component monosaccharides, together with the shift data, in assigning the 13C-spectra of 2 and 3. Atom positions were measured on Drieding models, and shifts calculated by using the axial symmetry approximation were in excellent agreement with the observed values. © 1979.