Synthesis And Characterization Of Serials Glycidyl Ether Modified β-Cyclodextrin Derivatives

β-cyclodextrin (β-CD) is comprised of seven glucose units throughα-1, 4 glycosidic bonds. As a result of this special arrangement of the functional groups in the cyclodextrin molecules, the cavity is relatively hydrophobic compared to water while the external faces are hydrophilic. Soβ-CD is one of the model host compound in supramolecular chemistry research field as a good enzyme-bottom international model system. Andβ-CD has been successfully used to enhance aqueous solubility of drugs, recognise organic molecules and separate chiral medicament isomers. However,β-CD in their native state is rigid molecules and offers limited utility in term of size shape ofβ-CD, water solubility and availability of chemically usefully functional groups. In order to increase water solubility and change its cavity's shape, chemical modification ofβ-CD is an available method to improve the physical and chemical characteristics ofβ-CD. Nowadays chemical modification ofβ-CD in common use is through primary hydroxyl groups at the C-6 positions and secondary hydroxyl groups at the C-2 and C-3 positions.Using phenyl glycidyl ether, 2-methylphenyl glycidyl ether, benzyl glycidyl ether andβ-CD as raw materials, novel glycidyl ether modifiedβ-cyclodextrin derivatives had been synthesized and separated.The experiments can be divided into two parts:1. Using phenyl glycidyl ether, 2-methylphenyl glycidyl ether andβ-CD as raw materials, novelβ-cyclodextrin derivatives had been synthesized in 1.5 % (w/v) and 30 % (w/v) sodium hydroxide solution. The products were isolated by using proper eluent 1-propanol: water: concd aq ammonia (6: 3: 1, V/V) through a self packed silica gel column chromatography, and their chemical structures were proved to be mono 2 substituted phenoxy, (2-methylphenoxy)-2-hydroxypropyl-β-cyclodextrin (a1, b1) and mono 6 substituted phenoxy, (2-methylphenoxy)-2-hydroxypropyl-β-cyclodextrin (A1, B1) by means of TLC, UV, IR, CD, DSC, MS, 1HNMR and 13CNMR measurements.2. Using benzyl glycidyl ether andβ-CD as raw materials, benzyloxy-2-hydroxypropyl-β-cyclodextrin was synthesized in 1.5 %, 3 %, 9%, 15%, 30% (w/v) sodium hydroxide solution at fixed molar ratio of raw material and reaction time, and their average substituted degrees were calculated by mass spectrometry method (MS) and nuclear magnetic resonance method (1HNMR). The influences of the reaction condition such as concentration of alkali solution on the average substituted degrees of benzyloxy-2-hydroxypropyl-β-cyclodextrin were studied in this paper.