Two novel amylose derivatives 2a and 2b bearing 4-tert-butylbenzoate at the 2-position and 3,5-dichlorophenylcarbamate/3-(triethoxysilyl)propylcarbamate residues at 3- and 6-positions were successfully synthesized and immobilized onto silica gel, and their chiral recognition abilities were evaluated as chiral packing materials (CPMs) for high-performance liquid chromatography. These immobilized CPMs exhibited recognition ability similar to conventional coated CPM, and for some racemates, comparable or better resolutions were observed even compared to commercial immobilized amylose- or cellulose-based columns.