Synthesis Of Multi-substitued β-cyclodextrin Deriatives And Their Molecular Recognition With Phenyl Cyclics Guests

β-cyclodextrin is cyclic oligosaccharides consisting of seven a-1,4-linked D-(t)-glucopyranose units and has hydrophobic cavity and hydrophilic outer, which make it can be used in many fields. However,β-cyclodextrin has low water solubility and some other shortcomings in physical and chemical properties, which limits its used fields. In order to enlarge the scope ofβ-cyclodextrin's application,β-cyclodextrin was modified in this paper, three types ofβ-cyclodextrin derivatives were synthesized, and molecular reconition was studied, as follows:1. 2-(3-propyloxy-2-hydroxy)propyl-β-cyclodextrin and 6-(3-propyloxy-2-hydro–xy)propyl-β-cyclodextrin were synthesized and isolated. Developing solvent of 1-propanol:water:concd aq ammonia (6:3:1,V/V) was used to isolate these products through a self packed silica gel column chromatography, and products were proved by means of the TLC, IR, DSC, MS, 1H NMR and 13C NMR measurements. (3-propyloxy-2-hydroxy)propyl-β-cyclodextrins were synthesized in different concentration of NaOH aqueous and their degrees of substitution were calculated by mass spectrometry method (MS) and nuclear magnetic resonance method. Molecular recognition of guest molecules (including p-amino-benzene sulfonic acid, p-nitrobenzoic acid,p-aminobenzoic acid,o-aminobenzoic acid,m-aminobenzoic acid) by these products andβ-cyclodextrin were studied by using UV spectra, it was indicated that molecular recognition canctants of (3-propyloxy -2-hydroxy) propyl-β-cyclodextrins were more than molecular recognition canctant ofβ-cyclodextrin.2. Synthesis and characterization of methylatedβ-cyclodextrin.β-cyclodextrin was dissolved in sodium hydroxide solution then dimethyl sulfate was dropped in the solution, reacted 6h at 60°C. Then product was obtained though vaccum distillation and characterized by IR, 1H NMR, MS measurements.3. Synthesis and characterization of (3-acyloxy-2-hydroxy)propyl-β-cyclodextrin. Glycidyl benzoate,glycidyl propionate,glycidyl acetate were obtained respectly through a phase-transfer catalytic methodology using sodium benzoate, sodium propionate, sodium acetate and epichlorohydrin as raw materials, and pure products were obtained though vaccum distillation.β-cyclodextrin and glycidyl benzoate, glycidyl propionate, glycidyl acetate, reacted in organic solvent and goal product were...