Sulfonate protecting groups. Improved synthesis of scyllo-inositol and its orthoformate from myo-inositol.
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%.
Sarmah
Manash P
MP
National Chemical Laboratory, Division of Organic Synthesis, Pune 411 008, India.
Shashidhar
Mysore S
MS
D007294:Inositol / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013451:Sulfonic Acids / Q000737:chemistry*
D013451:Sulfonic Acids; C009217:scyllitol; D007294:Inositol