C-Glycoside based mimics of d-myo-inositol 1,4,5-trisphosphate

Abstract Epimeric C -glycoside based polyphosphates, α- and β- d -glucopyranosylmethanol 3,4,1′-trisphosphates ( 8 and 9 ) were prepared from d -glucose. The key intermediate, allyl 2,6-di- O -benzyl-α- d -glucopyranoside, was prepared in five steps (67% yield) from allyl α- d -glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P 3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C -glycoside analogues are worthy of further development as Ins(1,4,5)P 3 receptor ligands.