Collect. Czech. Chem. Commun. 1984, 49, 1780-1787

Partial hydrolysis of acyl 1,6-anhydro-β-D-glucopyranose

Štefan Kučár, Juraj Zámocký, Juraj Zemek, Dušan Anderle and Mária Matulová

Institute of Chemistry, Center of Chemical Research, Slovak Academy of Sciences, 842 38 Bratislava


Partial hydrolysis of per-O-acetyl- and per-O-benzoyl derivatives of 1,6-anhydro-β-D-glucopyranose with methanolic hydrogen chloride and hydrazine hydrate was investigated. The acyl group at C(3) is of substantial influence on the course of hydrolysis. The esterified hydroxyl group at C(3) was found to be most stable on acid hydrolysis with methanolic hydrogen chloride when compared with that at C(2), or C(4); on the other hand, this ester group is the most labile upon hydrolysis with hydrazine hydrate. Selectivity of the respective ester groups towards hydrolysis made it possible to prepare all variations of acetyl and benzoyl derivatives of 1,6-anhydro-β-D-glucopyranose.