A new approach to the enantioselective synthesis of sitophiluse (4S, 5S)-isomer showing an attractant activity for maize weevil is considered. The monobenzyl ethers of diastereomesic triol prepared from commercially available (4R)-acetoxyacid were used as a key monochiral block in this synthesis. The synthesis conditions and the products separation technique are described in detail. The diastereomers obtained were separated using high-rate eluent liquid chromatography method, and characterized using IR, PMR, and mass-spectrometry techniques.