Regioselective hydrolysis of myo-inositol 1,3,5-orthobenzoate via a 1,2-bridged 2′-phenyl-1′,3′-dioxolan-2′-ylium ion provides a rapid route to the anticancer agent Ins(1,3,4,5,6)P5

Chemical Communications Pub Date: 2006-06-07 DOI: 10.1039/B605392K

Abstract

Acid hydrolysis of myo-inositol 1,3,5-orthobenzoate leads regioselectively to 2-O-benzoyl-myo-inositol via a 1,2-bridged 2′-phenyl-1′,3′-dioxolan-2′-ylium ion observed by 1H and 13C NMR spectroscopy, providing the precursor for a highly efficient route to the anticancer agent myo-inositol 1,3,4,5,6-pentakisphosphate.

Graphical abstract: Regioselective hydrolysis of myo-inositol 1,3,5-orthobenzoate via a 1,2-bridged 2′-phenyl-1′,3′-dioxolan-2′-ylium ion provides a rapid route to the anticancer agent Ins(1,3,4,5,6)P5
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