The preparation of intermediates for the synthesis of 1D-myo-inositol 1,4,5-trisphosphate, a second messenger for signal transduction in cells.
Racemic 1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol was prepared by a new route involving crotyl (but-2-enyl) ethers and converted into the (-)-omega-camphanates to give the pure crystalline 1L-diastereoisomer and the chirally impure, syrupy 1D-diastereoisomer. The latter was converted via the 1-O-allyl or 1-O-p-methoxybenzyl ethers into chirally pure 1D-2,3,6-tri-O-benzyl-myo-inositol [required as an intermediate for the synthesis of 1D-myo-inositol 1,4,5-trisphosphate (1,4,5-IP3)], which was also prepared by de-p-methoxybenzylation of 1D-2,3,6-tri-O-benzyl-1,5-di-O-p-methoxybenzyl-myo-inositol. Racemic 2,4-di-O-benzyl-5,6-O-isopropylidene-1-O-p-methoxybenzyl-myo-inositol was prepared in a similar way to the analogous tribenzyl ether (using crotyl ethers) and the omega-camphanate esters behaved similarly, allowing efficient resolution by crystallisation of the (-)- and (+)-omega-camphanates. Racemic 1,2,4-tri-O-allyl-3-O-(but-2-enyl)-myo-inositol was resolved via the (-)-omega-camphanates and was also converted into 1,2,4-tri-O-(cis-prop-1-enyl)-myo-inositol, an alternative intermediate for the synthesis of 1,4,5-IP3.
Desai
T
T
Laboratory of Lipid and General Chemistry, National Institute for Medical Research, Mill Hill, London, United Kingdom.
Gigg
J
J
Gigg
R
R
Payne
S
S
Penades
S
S
D000818:Animals; D002468:Cell Physiological Phenomena; D006801:Humans; D015544:Inositol 1,4,5-Trisphosphate / Q000138:chemical synthesis* / Q000502:physiology; D015394:Molecular Structure; D010766:Phosphorylation; D015290:Second Messenger Systems / Q000502:physiology*; D015398:Signal Transduction / Q000502:physiology*; D013237:Stereoisomerism
D015544:Inositol 1,4,5-Trisphosphate