Intramolecular Inhibition by Imidazole in Acid-Catalyzed Hydrolysis of Protected Carbohydrates

Published January 20, 2025 10:59

The study uncovers an anomaly in the acid-catalyzed hydrolysis of the 5,6-O-isopropylidene group in specific D-gluco- and D-allofuranose derivatives, linked to C3-epimers with 3-O-imidazole sulfonyl moieties. Advanced modeling reveals how interactions between protecting groups and steric effects inhibit this reaction, providing new insights into carbohydrate chemistry.

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