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• W2080770187 abstract "A highly chemoselective strategy for the synthesis of N,N,N-trimethyl chitosan (TMC) homopolymer and highly substituted N-alkyl-N,N-dimethyl chitosan derivatives was achieved using di-tert-butyldimethylsilyl-3,6-O-chitosan (di-TBDMS chitosan) as a precursor. The influence of different solvents, reagents and other reaction conditions on the reduction, trimethylation and quaternization of these di-TBDMS chitosan derivatives was studied. Products were characterized by NMR after each step. Di-TBDMS chitosan was reacted with methyl iodide in NMP, giving a 100% substituted TMC with the trimethyl group appearing at 3.35 ppm in 1H NMR spectrum. N-Propyl-, N-butyl- and N-hexyl-N,N-dimethyl chitosan derivatives were synthesized by stepwise reductive alkylation of di-TBDMS chitosan, followed by quaternization with dimethyl sulfate in dichloromethane, giving 65–72% substituted N-alkyl-N,N-dimethyl chitosan derivatives under optimized conditions. Analysis of these water-soluble chitosan derivatives by FT-IR, 1H NMR, 13C NMR, 1H–1H COSY and 1H–13C HSQC NMR enabled detailed structural characterization. All peaks could be assigned to N-modification, showing the selectivity of the di-TBDMS protection." @default.
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• W2080770187 date "2011-10-01" @default.
• W2080770187 modified "2023-10-17" @default.
• W2080770187 title "Synthesis of N,N,N-trimethyl chitosan homopolymer and highly substituted N-alkyl-N,N-dimethyl chitosan derivatives with the aid of di-tert-butyldimethylsilyl chitosan" @default.
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• W2080770187 doi "https://doi.org/10.1016/j.carbpol.2011.06.007" @default.
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