Various amino protecting groups influence on H-1 and C-13 chemical shifts in a 2-deoxy-2-amino glucopyranoside

One glycoside, pent-4-enyl 2-amino-3,4-di-O-benzoyl-6-O-t-butyldimethylsily l-2-deoxy-beta-D-glucopyranoside (1), has been derivatized at the amino fun ction into five related compounds: ammonium trifluoroacetate, N-acetyl, tet rachlorophthalimide, phthalimide and azide. The H-1 and C-13 NMR spectra of these compounds have been fully assigned and compared. Significant influen ce on the chemical shifts given by the amino functionality can be found in the pyranosidic ring at position 1,2 and 3. Only minor variations were foun d throughout the remaining positions.