35649-00-4Relevant academic research and scientific papers
Synthesis and Utilization of Trialkylammonium-Substituted Cyclodextrins as Water-Soluble Chiral NMR Solvating Agents for Anionic Compounds
Dowey, Alison E.,Puentes, Cira Mollings,Carey-Hatch, Mira,Sandridge, Keyana L.,Krishna, Nikhil B.,Wenzel, Thomas J.
, p. 299 - 305 (2016)
Cationic trialkylammonium-substituted α-, β-, and γ-cyclodextrins containing trimethyl-, triethyl-, and tri-n-propylammonium substituent groups were synthesized and analyzed for utility as water-soluble chiral nuclear magnetic resonance (NMR) solvating agents. Racemic and enantiomerically pure (3-chloro-2-hydroxypropyl)trimethyl-, triethyl-, and tri-n-propyl ammonium chloride were synthesized from the corresponding trialkyl amine hydrochloride and either racemic or enantiomerically pure epichlorohydrin. The ammonium salts were then reacted with α-, β-, and γ-cyclodextrins at basic pH to provide the corresponding randomly substituted cationic cyclodextrins. The 1H NMR spectra of a range of anionic, aromatic compounds was recorded with the cationic cyclodextrins. Cyclodextrins with a single stereochemistry at the hydroxy group on the (2-hydroxypropyl)trialkylammonium chloride substituent were often but not always more effective than the corresponding cyclodextrin in which the C-2 position was racemic. In several cases, the larger triethyl or tri-n-propyl derivatives were more effective than the corresponding trimethyl derivative at causing enantiomeric differentiation. None of the cyclodextrin derivatives were consistently the most effective for all of the anionic compounds studied.
New cationic hydrophilic and amphiphilic polysaccharides synthesized by one pot procedure
Nichifor, Marieta,Stanciu, Magdalena Cristina,Simionescu, Bogdan C.
experimental part, p. 965 - 975 (2011/12/21)
Synthesis of cationic polysaccharides carrying quaternary ammonium groups of various chemical structures was performed by one pot procedure involving the chemical modification of a neutral polysaccharide (dextran, pullulan) with an equimolar mixture epichlorohydrin/tertiary amine, in aqueous media. Study of the reaction mechanism showed that the quaternization reagent was the glycidyl derivative of the tertiary amine formed in situ. Formation of cationic polysaccharides and their chemical structure were confirmed by elemental analysis, potentiometric titration, FT-IR and NMR spectroscopy. The reaction efficiency of the one pot procedure was similar to other methods using preformed clorohydroxypropyl or glycidyl quaternary ammonium reagents, but gave better results for the introduction of quaternary ammonium groups with more hydrophobic substituents. The procedure allowed the synthesis of a large variety of hydrophilic and amphiphilic cationic polysaccharides with potential application as hipolipemic drugs, flocculants or antibacterial agents.
