Cookies on this website

We use cookies to ensure that we give you the best experience on our website. If you click 'Accept all cookies' we'll assume that you are happy to receive all cookies and you won't see this message again. If you click 'Reject all non-essential cookies' only necessary cookies providing core functionality such as security, network management, and accessibility will be enabled. Click 'Find out more' for information on how to change your cookie settings.

Two routes for the synthesis of the myo-inositol 1,4,5-triphosphate analogue myo-inositol 1-phosphorothioate 4,5-bisphosphate have been devised. DL-2,3,6-Tri-O-benzyl-1-O-(cis-prop-1-enyl)-myo-inositol was prepared from DL-1-O-allyl-2,3,6-tri-O-benzyl-myo-inositol and phosphorylated to the protected 4,5-biphosphate. Removal of the propenyl group generated DL-1,2,4-tri-O-benzyl-5,6-bis[bis(2-cyanoethoxy)phospho]-myo-inositol which was thiophosphorylated to give DL-2,3,6-tri-O-benzyl-1-O-[bis(2-cyanoethoxy)thiophospho]-4,5-bis[bis(2-cyanoethoxy)phospho]-myo-inositol. Deblocking afforded racemic myo-inositol 1-phosphorothioate 4,5-bisphosphate, which was reacted with the iodoketone of a fluorescent label to generate a fluorescently labelled inositol 1,4,5-trisphosphate analogue. DL-1-O-Allyl-2,3,6-tri-O-benzyl-myo-inositol was resolved into its enantiomers by means of the crystalline 4,5-biscamphanate ester. 1 D-(+)-1-O-Allyl-2,3,6-tri-O-benzyl-myo-inositol was used to prepare D-myo-inositol 1-phosphorothioate 4,5-bisphosphate in a fashion analogous to the racemic modification via1 D-(+)-2,3,6-tri-O-benzyl-1-O-(cis-prop-1-enyl)-4,5-bis[bis(2-cyanoethoxy)phospho]-myo-inositol. In a second route, DL-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol was converted into the corresponding 4,5-dibutyrate. Removal of the isopropylidene group gave DL-1,4,-di-O-benzyl-5,6-di-O-butyryl-myo-inositol which was converted into the corresponding 1-O-p-methoxybenzyl ether via the 1,2-O-dibutylstannylidene derivative. Benzylation of the 2-position and removal of the butyrates yielded DL-1-O-p-methoxybenzyl-2,3,6-tri-O-benzyl-myo-inositol which was phosphorylated to DL-1-O-p-methoxybenzyl-2,3,6-tri-O-benzyl-4,5-bis[bis(2-cyanoethoxy)phospho]-myo-inositol. Removal of the p-methoxybenzyl group gave the key intermediate DL-1,2,4-tri-O-benzyl-5,6-bis[bis(2-cyanoethoxy)phospho]-myo-inositol, which could be further elaborated to myo-inositol 1-phosphorothioate 4,5-bisphosphate. © Royal Society of Chemistry.

Original publication




Journal article


Journal of the Chemical Society, Perkin Transactions 1

Publication Date



2899 - 2906