The preparation of intermediates for the synthesis of 1D-myo-inositol 1,4,5-trisphosphate, a second messenger for signal transduction in cells
| Autor: | Roy Gigg, Jill Gigg, Trupti Desai, Soledad Penades, Sheila Payne |
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| Rok vydání: | 1992 |
| Předmět: |
Stereochemistry
Cyclitol Ether Stereoisomerism Inositol 1 4 5-Trisphosphate Biochemistry Second Messenger Systems Analytical Chemistry law.invention Cell Physiological Phenomena Crotyl chemistry.chemical_compound law Molecule Animals Humans Crystallization Phosphorylation Molecular Structure Organic Chemistry Diastereomer General Medicine chemistry Second messenger system Signal Transduction |
| Zdroj: | Carbohydrate research. 234 |
| ISSN: | 0008-6215 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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