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.
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.
Godage
Himali Y
HY
Wolfson Laboratory of Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
Riley
Andrew M
AM
Woodman
Timothy J
TJ
Potter
Barry V L
BV
D000143:Acids / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D007295:Inositol Phosphates / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism
D000143:Acids; D000970:Antineoplastic Agents; D007295:Inositol Phosphates; C013571:inositol pentaphosphate