Further insight for the synthesis of 6‐amino‐6‐deoxy amylose

Abstract

AbstractBecause 6‐amino‐6‐deoxy amylose is an important intermediate for many materials, developing a practical pathway to easily prepare it in bulk is of significance. The synthesis of 6‐amino‐6‐deoxy amylose included three reactions. In the chlorination reaction, the crude product could be fully de‐esterified under the improved conditions, and the reaction mechanism was re‐understood. The azido group was reduced with sodium borohydride in which the reaction conditions were studied in detail. With the improved synthetic pathway, 6‐amino‐6‐deoxy amylose could be easily prepared. The 6‐amino‐6‐deoxy amylose was characterized via its benzamide derivative with 1H NMR, 1H‐13C HSQC NMR, and 1H‐1H COSY NMR, confirming the hydroxyl group at C6 of amylose was converted to amino group with a degree of substitution of 98.2%. Additionally, the 6‐amino‐6‐deoxy amylose was analyzed toward iodine reagent and X‐ray diffraction, and the corresponding results showed that it was different from amylose in suprastructure and crystal structure.