Acetic Anhydride → alpha-D-Glucopyranosyl pentaacetate

Participants

Reaction Steps

Analogously to what is described for the synthesis of title compound 70a, the reaction of 100 g (555.0 mmol) of α-D-glucopyranose with a mixture that consists of 1000 ml of absolute pyridine and 1000 ml of acetic acid anhydride after working-up and recrystallization from 95% aqueous ethanol yields 190.6 g (88.0%) of the above-mentioned title compound as a colorless and crystalline compound. By 1H-NMR-spectroscopic study of the thus obtained title compound, it was possible to determine the a to β ratio of two possible anomers at ≧98:2. The title compound accordingly is the exclusively α-configured anomer.

Provenance & Evidence