The transfer of an acyl group from glucose penta-acetate to methanol, n-amylamine, and n-amyl mercaptan with imidazole catalysis has been observed and studied with the aid of PMR spectroscopy. Through rate studies of the reaction between glucose penta-acetate and methanol in the presence of imidazole, and as a result of the observation of imidazole-catalyzed epimerization of β- to α-glucose penta-acetate, a mechanism for the transacetylation reaction has been proposed. The possibility that this mechanism can be applied to enzyme catalyzed physiological transacetylations is discussed.