一种简便、有效的合成6－OTs－β－CD的新方法

A Convenient and Efficient Method of Tosylation of β-Cyclodextrin in Tetrahydrofuran-Water

一种简便、有效的合成６－ＯＴｓ－β－ＣＤ的新方法刘育，张毅民，孙世新，陈荣悌（南开大学化学系，天津，３０００７１）关键词β－环糊精，６－ＯＴｓ－β－环糊精，合成天然的和人工合成的β－环糊精（简称β－ＣＤ）在模拟酶和超分子体系的分子识别方面［１，２］倍...

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, IR and 1H NMR spectra. The results indicated that higher yield of 6-OTs-β-CD was obtained and the use of toxic pyridine was circumvented.