SUCROSE OCTABENZOATE - ASSIGNMENT OF C-13 AND H-1 RESONANCES OF THE SUCROSE MOIETY AND THE C-13 RESONANCES OF THE CARBONYL CARBONS - USE OF C-13 NMR-SPECTROSCOPY FOR THE STUDY OF SELECTIVE DEACYLATION

Assignment of the 1H and 13C signals arising from the carbohydrate portion of sucrose octabenzoate has been achieved using homonuclear shift correlation experiments (COSY) and one-bond 1H-13C heteronuclear shift correlation measurements, respectively. The 13C resonances of the carbonyl carbon atoms of the eight benzoyl groups are readily distinguished for solutions in benzene-d6-pyridine-d5 (1:1), and have been assigned by means of three-bond 1H-13C shift correlation studies coupled with measurement of the 13C-n.m.r. spectrum of a sucrose octabenzoate specifically labelled with 13C in some of the carbonyl groups. With this assignment, products of partial deacylation of the octabenzoate may readily be identified by treatment with excess of benzoyl-carbonyl-13C chloride followed by measurement of the 13C-n.m.r. spectrum of the labelled sucrose octabenzoate, so prepared, in the carbonyl region. © 1990.