title: Regioselective deprotection of orthobenzoates for the synthesis of inositol phosphates.
abstract: Synthetic myo-inositol 1,4,5-triphosphate, Ins(1,4,5)P(3), and myo-inositol 1,3,4,5-tetraphosphate, Ins(1,3,4,5)P(4), continue to be valuable in biological studies. Inositol orthoesters have proved an important class of intermediate to access these compounds. We investigated the ability of steric bulk from a 4-O protecting group to direct DIBAL-H reduction of inositol orthobenzoates to generate the natural Ins(1,4,5)P(3) precursor 2,3,6-O-tribenzyl myo-inositol. Introduction of an equatorial 4-C-methyl group imparts totally selective reduction and we report the synthesis of novel 4-C-methyl-Ins(1,4,5)P(3) and 4-C-methyl-Ins(1,3,4,5)P(4).
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington Campus, SW7 2AZ, UK.
authors.forename: Joanna M
authors.initials: JM
authors.lastname: Swarbrick
authors.forename: Samuel
authors.initials: S
authors.lastname: Cooper
authors.forename: Geert
authors.initials: G
authors.lastname: Bultynck
authors.forename: Piers R J
authors.initials: PR
authors.lastname: Gaffney