SYNTHESIS OF OPTICALLY ACTIVE DERIVATIVES OF MYO-INOSITOL - PREPARATION OF 1 L-MYO-INOSITOL 1-PHOSPHATE

1 l-1-O-toluene-p-sulphonyl-chiro-inositol 5 has been prepared by the selective de-O-methylation and de-cyclohexylidenation of 1l-3,4:5,6-di-O-cyclohexylidene-2-O-methyl-1-O-toluene-p-sulphonyl-chiro -inositol obtained from quebrachitol, 1l-2-O-methyl-chiro-inositol. This optically active toluene-p-sulphonyl derivative, which is by inversion at C-1, a potential source of optically active myo-inositol derivatives, has, after benzoylation, been converted into a mixture of 1d-1,2,4,5,6-penta-O-benzoyl-myo-inositol and 1,3,4,5,6-penta-O-benzoyl-myo-inositol, which were separated. From the former, after phosphorylation and debenzoylation, 1l-myo-inositol 1-phosphate, the product of the enzyme, glucose 6-phosphate-inositol 1-phosphate cyclase, was obtained as the crystalline dicyclohexylamine salt. © 1969.