Chiral synthesis of D- and L-myo-inositol 1,4,5-trisphosphate.
Chiral inositols (D-chiro-inositol from D-pinitol and L-chiro-inositol from L-quebrachitol) were converted to the 3,4-di-O-benzyl ethers, which were selectively benzoylated to yield the 1,2,5-tri-O-benzoyl-3,4-di-O-benzyl-chiro-inositols. The free hydroxyl group in each derivative was inverted by way of the trifluoromethane sulfonate ester to provide D- and L-1,2,4-tri-O-benzoyl-5,6-di-O-benzyl-myo-inositol. Hydrogenolysis to remove the benzyl ether groups gave the enantiomeric 1,2,4-tri-O-benzoyl-myo-inositols, which were phosphorylated by a dibenzylphosphite triester method. After hydrogenolysis and saponification of the derivatives, the D- and L-myo-inositol 1,4,5-trisphosphates were isolated as the crystalline cyclohexylammonium salts in gram quantity.
Tegge
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Department of Biochemistry, University of California, Berkeley 94720.
Ballou
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D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D015544:Inositol 1,4,5-Trisphosphate; D007295:Inositol Phosphates / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009904:Optical Rotation; D013237:Stereoisomerism; D013403:Sugar Phosphates / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D007295:Inositol Phosphates; D013403:Sugar Phosphates; D015544:Inositol 1,4,5-Trisphosphate