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In order to develop new type of chiral separation materials, in this study, 6‐amino‐6‐deoxyamylose was used as chiral starting material with which 10 derivatives were synthesized. The amino group in 6‐amino‐6‐deoxyamylose was selectively acylated and then the hydroxyl groups were carbamoylated yielding amylose 6‐amido‐6‐deoxy‐2,3‐bis(phenylcarbamate)s, which were employed as chiral selectors (CSs) for chiral stationary phases of high‐performance liquid chromatography. The resulted 6‐amido‐6‐deoxyamyloses and amylose 6‐amido‐6‐deoxy‐2,3‐bis(phenylcarbamate)s were characterized by IR, 1H NMR, and elemental analysis. Enantioseparation evaluations indicated that most of the CSs demonstrated a moderate chiral recognition capability. The 6‐nonphenyl (6‐nonPh) CS of amylose 6‐cyclohexylformamido‐6‐deoxy‐2,3‐bis(3,5‐dimethylphenylcarbamate) showed the highest enantioselectivity towards the tested chiral analytes; the phenyl‐heterogeneous (Ph‐hetero) CS of amylose 6‐(4‐methylbenzamido)‐6‐deoxy‐2,3‐bis(3,5‐dimethylphenylcarbamate) baseline separated the most chiral analytes; the phenyl‐homogeneous (Ph‐homo) CS of amylose 6‐(3,5‐dimethylbenzamido)‐6‐deoxy‐2,3‐bis(3,5‐dimethylphenylcarbamate) also exhibited a good enantioseparation capability among the developed CSs. Regarding Ph‐hetero CSs, the enantioselectivity depended on the combination of the substituent at 6‐position and that at 2‐ and 3‐positions; as for Ph‐homo CSs, the enantioselectivity was related to the substituent at 2‐, 3‐, and 6‐positions; with respect to 6‐nonPh CSs, the retention factor of most analytes on the corresponding CSPs was lower than that on Ph‐hetero and Ph‐homo CSPs in the same mobile phases, indicating π–π interactions did occur during enantioseparation. Although the substituent at 6‐position could not provide π–π interactions, the 6‐nonPh CSs demonstrated an equivalent or even higher enantioselectivity compared with the Ph‐homo and Ph‐hetero CSs.

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