Acetic Anhydride → 1,2,3,4,6-Penta-O-acetyl-D-mannopyranose

Participants

Reaction Steps

Analogously, as described in the literature [M. L. Wolfrom and A. Thompson in Methods in Carbohydrate Chemistry (R. L. Whistler, M. L. Wolfrom and J. N. BeMiller, Eds.), Academic Press, New York, Vol. II, 53, pp. 211-215, (1963)], the reaction of 150 g (832.5 mmol) of α,β-D-mannopyranose with a mixture that consists of 1500 ml of absolute pyridine and 1500 ml of acetic acid anhydride after working-up yields 315 g (96.7%) of the above-mentioned title compound as crude product in the form of a viscous and colorless oil. By 1H-NMR-spectroscopic study of the thus obtained title compound, it was possible to determine the α to β ratio of both anomers at 4:1. A separation of the α,β-anomers of the above-mentioned title compound can thus be eliminated in performing the subsequent reaction steps.

Provenance & Evidence