SYNTHESIS AND N.M.R.-SPECTRAL ANALYSIS OF UNENRICHED AND -ENRICHED 5-DEOXYPENTOSES AND 5-O-METHYLPENTOSES

Article abstract of DOI:10.1016/0008-6215(87)80180-5

Chemical methods are described for preparing unenriched and <1-13C>-enriched 5-deoxy- and 5-O-methyl-pentoses in the D or L configuration.The 1H-n.m.r.-spectra of these compounds have been interpreted, and the 13C n.m.r. spectra assigned with the aid of 2-D 13C-1H chemical-shift correlation spectroscopy.Tautomeric forms (furanoses, hydrate, and aldehyde) in solution in 2H2O have been quantified with the aid of <1-13C>-enriched derivatives.Spectra of 5-deoxypentoses, and methyl pentofuranosides have been compared, in order to assess the effect of 5-C-deoxygenation and 5-O-methylation on chemical shifts and coupling constants (1H-1H, 13C-1H, and 13C-13C) and on the pentofuranose conformations.