- A convenient synthesis of D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3) and L-myo-inositol 1,4,5-trisphosphate (Ins(3,5,6)P3)
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An efficient synthesis of an optically active inositol derivative that is a precursor to D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3, (-)) is described. Crystallization of the diastereomers of (±) -1-O-[(+)- menthoxycarbonyl]-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol diastereomers from methanol gives only one diastereomer. Alkaline hydrolysis gives the useful inositol derivative (-)-6-O-benzyl-2,3:4,5-di-O- isopropylidene-myo-inositol. Likewise, crystallization of the diastereomers of (±)-3-O-[(-)-menthoxycarbonyl]-4-O-benzyl-1,2:5,6-di-O-isopropylidene- myo-inositol from methanol gave a pure compound which could be hydrolyzed to give (+)-4-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol, a precursor to D-myo-inositol 3,5,6-trisphosphate (Ins(3,5,6)P3, (+)). The ease with which these enantiomerically pure inositol derivatives were isolated may facilitate the synthesis of more complex inositol phosphate derivatives such as D-myo- inositol 1,3,4,5-tetrakisphosphate.
- Leung, Lawrence W.,Bittman, Robert
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p. 171 - 179
(2007/10/03)
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- The regioselective synthesis of enantiomerically pure myo-inositol derivatives. Efficient synthesis of myo-inositol 1,4,5-trisphosphate
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Regioselective 1-O-acylation of myo-inositol and simultaneous optical resolution has been achieved by perborylation, transmetallation using di-n-butyltin-bis-acetylacetonate and then acylation with (-)-menthyl chloroformate. Diastereomerically pure 1-O-(-
- Aguilo, Agustin,Martin-Lomas, Manuel,Penades, Soledad
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p. 401 - 404
(2007/10/02)
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