156556-46-6Relevant articles and documents
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
Godage, Himali Y.,Riley, Andrew M.,Woodman, Timothy J.,Potter, Barry V. L.
, p. 2989 - 2991 (2006)
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 hi
Synthesis of 2-diphospho-myo-inositol 1,3,4,5,6-pentakisphosphate and a photocaged analogue
Pavlovic,Thakor,Jessen
, p. 5559 - 5562 (2016/07/06)
Diphosphoinositol polyphosphates (inositol pyrophosphates, X-InsP7) are a family of second messengers with important roles in eukaryotic biology. Their chemical synthesis and modification remains a challenging task due to the high density of ph
Regioselective opening of myo-inositol orthoesters: Mechanism and synthetic utility
Godage, Himali Y.,Riley, Andrew M.,Woodman, Timothy J.,Thomas, Mark P.,Mahon, Mary F.,Potter, Barry V. L.
, p. 2275 - 2288 (2013/04/24)
Acid hydrolysis of myo-inositol 1,3,5-orthoesters, apart from orthoformates, exclusively affords the corresponding 2-O-acyl myo-inositol products via a 1,2-bridged five-membered ring dioxolanylium ion intermediate observed by NMR spectroscopy. These C-2-substituted inositol derivatives provide valuable precursors for rapid and highly efficient routes to 2-O-acyl inositol 1,3,4,5,6-pentakisphosphates and myo-inositol 1,3,4,5,6-pentakisphosphate with biologically interesting and anticancer properties. Deuterium incorporation into the α-methylene group of such alkyl ester products (2-O-C(O)CD 2R), when the analogous alkyl orthoester is treated with deuterated acid, is established utilizing the novel orthoester myo-inositol 1,3,5-orthobutyrate as an example. Such deuterated ester products provide intermediates for deuterium-labeled synthetic analogues. Investigation into this selective formation of 2-O-ester products and the deuterium incorporation is presented with proposed mechanisms from NMR experiments.
