Abstract
The reaction of cellulose with N-carbonyl α-amino acid ester 1 leading to cellulose carbamate 2 was carried out in N,N-dimethylacetamide at 100 °C. For N-carbonyl L-leucine ethyl ester (1a), the degree of the carbamate substituent (DS) in 2a was 2.5 for [1a]/[glucose units in cellulose] = 3.0 and reached ca. 3.0 for [1a]/[glucose units in cellulose] = 4.0. Cellulose carbamate 2a was highly soluble in not only aprotic polar solvents but also other organic solvents such as ethyl ether and methyl alcohol. The chiral discrimination ability of 2a was higher than those of the cellulose carbamates having L-phenylalanine and L-aspartic acid moieties.
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