A study of chromatographic enantioseparation in the synthesis of dl- myo-inositol derivatives by HPLC is presented. All intermediates in the synthesis of fully protected dl- myo-inositol 1,4,5-triphosphate and some isomers thereof could be separated using a commercially available analytical β-cyclodextrin-bonded column. The retention behavior of the inositol derivatives under reversed-phase conditions using methanol and acetonitrile as organic modifiers was investigated. In contrast to fully protected myo-inositol derivatives, the fully protected myo-inositol phosphates could be separated. Although enantiomeric separations were successful in the majority of cases, anticipation of chiral recognition for the derivatives is complicated. In knowledge of our results successful separation requires a benzyl ether and/or a cyclohexylidene ketal.