Eight new optically pure calixarenyl derivatives, in which their lower rims were substituted with Evans oxazolidinone or pyranose moieties, were desbribed. All macrocycles were fully characterized by NMR spectroscopy, optical rotation and elemental analysis. Introduction of chiral auxiliaries reduced the symmetry of the macrocycle as observed by NMR. Stereospecific alkylation on the Evans oxazolidinone moiety allowed the asymmetric introduction of a methyl substituent near a phenolic position of the marocylcle.