REACTIONS OF THE KETONE DERIVED FROM (+/-)-3,4,5-TRI-O-BENZYL-1,2-O-ISOPROPYLIDENE-MYO-INOSITOL - PREPARATION OF RACEMIC DERIVATIVES OF EPI-INOSITOL AND OF 4-C-METHYL-EPI-[(+/-)-ISO-LAMINITOL] AND 4-C-METHYL-MYO-INOSITOL [(+/-)-LAMINITOL]

摘要

Oxidation of (+/-)-3,4,5-tri-O-benzyl-1,2-O-isopropylidene-myo-inositol with the pyridine-SO3 complex in methyl sulfoxide gave the ketone which was reduced with sodium borohydride to give almost exclusively the corresponding epi-inositol derivative. Reaction of the ketone with diazomethane gave an epoxide which was reduced with lithium aluminium hydride to give a 4-C-methyl-myo-inositol derivative and reaction of the ketone with methyl magnesium iodide gave the isomeric 4-C-methyl-epi-inositol derivative. (C) 1997 Elsevier Science Ltd. [References: 27]