Objective To study the optimization conditions for Sharpless asymmetric epoxidation-based synthesis of chiral glycidyl alcohols and their phosphoester compounds. Methods With allyl alcohol as the starting material， we synthesized alkynyl， phenyl， and alkyl （3b ~ 8b）substituted chiral glycidyl alcohols， followed by treatment with diphenyl chlorophosphate for corresponding phosphoester derivatives （3c ~ 5c，8c）. We characterized the structures of the compounds by 1H nuclear magnetic resonance （NMR）， 13C NMR， 31P NMR， and mass spectrometry， measured their enantiomeric excess （ee） values by chiral high-performance liquid chromatography， and preliminarily evaluated their antitumor activities. Results Ten chiral glycidyl alcohols with different substitutions and their phosphoester derivatives were synthesized. Antitumor activity tests showed that some of the compounds had inhibitory effects on the proliferation of HeLa cells， 231 cells， and HepG2 cells. Conclusion We established optimization conditions for Sharpless asymmetric epoxidation and chiral glycidyl alcohol phosphoesterification， providing a reference for expanding the application of the Sharpless method.