Synthesis of an unsaturated mixed-acid phosphatidylinositol of natural configuration. A new procedure for resolving racemic alcohols
✍ Scribed by Jul.G. Molotkovsky; L.D. Bergelson
- Book ID
- 103040643
- Publisher
- Elsevier Science
- Year
- 1973
- Tongue
- English
- Weight
- 559 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
DL-1,2,4,5,6-Penta-O-acetyl-myo-inositol was resolved into antipodes through the salts of its acid oxalate with quinidine and (-)-t~-phenethylamine. The optically active pentaacetates were regenerated from the oxalates by lead tetraacetate oxidation. The optical purity of these pentaacetates was confirmed by their transformation into optically pure ID-and 1L-myoinositol l-phosphates. The 1D-isomer of the pentaacetate was used as starting compound for the synthesis of a mixed acid phosphatidylinositol having the natural configuration at all the asymmetric centres and the normally predominating l-saturated 2-unsaturated distribution of the fatty acid residues. From the lL-pentaacetate an isomer of phosphatidylinositol with the unnatural 1 L-configuration of the rnyo-inositol residue has been obtained. * The recommended rules of lipid and cyclitol nomenclature [ 121 are used in this paper.