Chem. J. Chinese Universities ›› 1995, Vol. 16 ›› Issue (10): 1567.
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LIU Yu, ZHANG Yi-Min, SUN Shi-Xin, CHEN Rong-Ti
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Abstract: 6-o-tosyl-β-cyclodextrin(6-OTs-β-CD)was prepared by the reaction of β-CD with p-toluenesulfonyl chloride in the presence of potassium hydroxide using tetrahydrofuran-water(1:1)as the solvent.Potassium hydroxide(0.4 g) and β-cyclodextrin (10g)dissloved in water(100mL)-tetrahydrofuran (70mL) were placed in a flask(250 mL) and the mixture was stirred about 15 min under a nitrogen gas at the room temperature. To the mixture was added dropwise p-toluenesulfonyl chloride(1.68g) in THF (30mL) for 1.5h, and the solution was stirred continuously for 3 h.Then the solution was poured into acetone(40 mL).After having been placed for enough time in the icebox, the solid was filtered, washed with water, dried, and washed with ether thoroughly, and then recrystallized twice from water to give pure product 4.5g(37.6%).The compound has been characterized by means of elemental analysis, UVF-Vis, IRand 1HNMR spectra. The results indicated that higher yield of 6-OTs-β-CD was obtained and the use of toxic pyridine was circumvented.
Key words: β-Cyclodextrin(β-CD), 6-OTs-β-CD, Tosylation
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LIU Yu, ZHANG Yi-Min, SUN Shi-Xin, CHEN Rong-Ti. A Convenient and Efficient Method of Tosylation of β-Cyclodextrin in Tetrahydrofuran-Water[J]. Chem. J. Chinese Universities, 1995, 16(10): 1567.
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