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The preparation of 2,3,6-O-tribenzyl- and 2,6-O-dibenzyl-myo-inositols with beta-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)P(3) and Ins(1,3,4,5)P(4) 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 InsP(3) and InsP(4) 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 publication

DOI

10.1021/jo100414e

Type

Journal article

Journal

J Org Chem

Publication Date

02/07/2010

Volume

75

Pages

4376 - 4386

Keywords

Inositol 1,4,5-Trisphosphate, Molecular Structure, Organophosphorus Compounds, Stereoisomerism, Structure-Activity Relationship