One-Pot Regioselective Diacylation of Pyranoside 1,2-cis Diols
Taeok Kim1, Michael R Bell1, V Narasimharao Thota1
1Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada, T6G 2G2.
Abstract:
A one-pot strategy for functionalizing pyranoside 1,2-cis-diols with two different ester protecting groups is reported. The approach employs regioselective acylation via orthoester hydrolysis promoted by a carboxylic acid, e.g., levulinic acid, acetic acid, benzoic acid, or chloroacetic acid. Upon removal of water and introduction of a coupling agent, the carboxylic acid is esterified to the hydroxyl group liberated during hydrolysis. Although applied to 1,2-cis-diols on pyranoside scaffolds, the method should be applicable to such motifs on any six-membered ring.
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