Basic study for acyl chitosan isothiocyanates synthesis by model experiments using glucosamine derivatives

Add time:07/19/2019    Source:sciencedirect.com

Affecting factors to the acyl chitosan isothiocyanate synthesis by N-phenylthiocarbamoylation and the following acylation was investigated using octyl 2-amino-2-deoxy-β-D-glucopyranoside as a model compound. It was found from the acetylation of N-phenylthiocarbamoyl glucosamine derivative with acetic anhydride/pyridine that the glucosamine isothiocyanate was formed via N,N-(acetyl)phenylthiocarbamoyl glucosamine derivative and the conversion of N,N-(acetyl)phenylthiocarbamoyl glucosamine derivative to the glucosamine isothiocyanate proceeded mainly by thermal degradation of N,N-(acetyl)phenylthiocarbamoyl groups. The reaction temperature was an important factor to the isothiocyanate synthesis. On the other hand, it was found from the acetylation of N-ethylthiocarbamoyl derivative (or N-allylthiocarbamoyl derivative) with acetic anhydride/pyridine that the glucosamine isothiocyanate was also prepared from N-ethylthiocarbamoyl glucoamine derivative (or N-allylthiocarbamoyl glucosamine derivative), but that N-phenylthiocarbamoylation was more preferable to the isothiocyanate synthesis than N-ethylthiocarbamoylation and N-allylthiocarbamoylation. Then, acylation products of N-phenylthiocarbamoyl chitosan (N,N-(hexanoyl)phenylthiocarbamoyl chitosan hexanoate or hexanoyl chitosan isothiocynate) could be controlled by the reaction temperature and reaction system.

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