Synthesis of 4-C-Alkyl Inositol 1,4,5-Trisphosphates and 1,3,4,5-Tetrakisphosphates

Joanna M. Swarbrick, Piers R. J. Gaffney

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The preparation of 2,3,6-O-tribenzyl- and 2,6-O-dibenzyl-myo-inositols with β-primary, secondary, and tertiary 4-C-alkyl or aryl groups is reported. Five of these novel polyols are elaborated to 4-C-alkyl Ins(1,4,5)P3 and Ins(1,3,4,5)P4 analogues. Regio- and stereoselective introduction of 4-C-alkyl or aryl substituents proceeded via a 4-exo-methylene oxide. Subsequent regioselective reduction of an orthobenzoate provided a divergent method to access both InsP3 and InsP4 precursors. Previously unreported phosphorylation of the tertiary hydroxyl and global deprotection afforded novel analogues that retain their full complement of polar and charged binding features.
Original languageEnglish
Pages (from-to)4376-4386
Number of pages11
JournalJournal of Organic Chemistry
Volume75
Issue number13
Early online date27 May 2010
DOIs
Publication statusPublished - 2 Jul 2010

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