Regioselective deprotection of orthobenzoates for the synthesis of inositol phosphates

Joanna M. Swarbrick, Samuel Cooper, Geert Bultynck, Piers R. J. Gaffney

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Synthetic myo-inositol 1,4,5-triphosphate, Ins(1,4,5)P3, and myo-inositol 1,3,4,5-tetraphosphate, Ins(1,3,4,5)P4, 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)P3 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)P3 and 4-C-methyl-Ins(1,3,4,5)P4.
Original languageEnglish
Pages (from-to)1709 - 1715
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number8
Early online date6 Mar 2009
DOIs
Publication statusPublished - 21 Apr 2009

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