Sulfonate protecting groups. Improved synthesis of scyllo-inositol and its orthoformate from myo-inositol |
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Authors: | Sarmah Manash P Shashidhar Mysore S |
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Institution: | National Chemical Laboratory, Division of Organic Synthesis, Pune 411 008, India. |
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Abstract: | A convenient high yielding method for the preparation of scyllo-inositol and its orthoformate from myo-inositol, without involving chromatography is described. myo-Inositol 1,3,5-orthoformate was benzoylated to obtain 2-O-benzoyl-myo-inositol 1,3,5-orthoformate. This diol was tosylated and the benzoyl group removed by aminolysis in a one-pot procedure to obtain 4,6-di-O-tosyl-myo-inositol 1,3,5-orthoformate. Swern oxidation of the ditosylate, followed by sodium borohydride reduction and methanolysis of tosylates gave scyllo-inositol 1,3,5-orthoformate (isolated as the triacetate). Aminolysis of the acetates followed by acid hydrolysis of the orthoformate moiety with trifluoroacetic acid gave scyllo-inositol in an overall yield of 64%. |
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Keywords: | Cyclitol Inositol Inositol phosphate Orthoesters Sulfonates Signal transduction |
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