Sökning: onr:"swepub:oai:lup.lub.lu.se:6cadb94f-f8bd-461f-8223-5d2082bbfc96" >
Synthesis of N,N,N-...
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
-
Benediktsdottir, Berglind E. (författare)
-
Gaware, Vivek S. (författare)
-
- Runarsson, Ögmundur (författare)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
-
visa fler...
-
Jonsdottir, Sigriaur (författare)
-
Jensen, Knud J. (författare)
-
Masson, Mar (författare)
-
visa färre...
-
(creator_code:org_t)
- Elsevier BV, 2011
- 2011
- Engelska.
-
Ingår i: Carbohydrate Polymers. - : Elsevier BV. - 0144-8617. ; 86:4, s. 1451-1460
- Relaterad länk:
-
http://dx.doi.org/10...
-
visa fler...
-
https://lup.lub.lu.s...
-
https://doi.org/10.1...
-
visa färre...
Abstract
Ämnesord
Stäng
- 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 H-1 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, H-1 NMR, C-13 NMR, H-1-H-1 COSY and H-1-C-13 HSQC NMR enabled detailed structural characterization. All peaks could be assigned to N-modification, showing the selectivity of the di-TBDMS protection. (C) 2011 Elsevier Ltd. All rights reserved.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- Chitosan
- tert-Butyldimethylsilyl
- Deprotection
- Stepwise reductive
- alkylation
- Quaternary chitosan
- Trimethyl chitosan
Publikations- och innehållstyp
- art (ämneskategori)
- ref (ämneskategori)
Hitta via bibliotek
Till lärosätets databas