20220315 Lowary TL Epub

One-Pot Regioselective Diacylation of Pyranoside 1,2-cis Diols

One-Pot Regioselective Diacylation of Pyranoside 1,2-cis Diols

J Org Chem. 2022 Apr 1 ;87(7):4894-4907.
doi: 10.1021/acs.joc.2c00252

閱讀文章

Kim T, Bell MR, Thota VN, Lowary TL*

摘要

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.