6-OTs-β-环糊精的合成工艺进展  

Progress in Synthesis of 6-OTs-β-Cyclodextrin

作　　者：张毅民[1] 刘春阳[1] 王学功[1] 万先凯[1] 王轶伟[1] 

机构地区：[1]绿色合成与转化教育部重点实验室天津大学化工学院,天津300072

出　　处：《化学工业与工程》2006年第6期539-543,共5页Chemical Industry and Engineering

摘　　要：6-对甲苯磺酰基-β-环糊精(6-OTs--βCD)作为合成环糊精6位单取代衍生物的中间产物受到了化学家们的广泛关注。对6-OTs--βCD的合成方法进行了论述,讨论了各种方法的优缺点,指出以吡啶为溶剂制备6-OTs--βCD的方法成熟,异构体少,但产率低,反应时间长,溶剂毒性大,后处理麻烦。同时,溶剂和反应器都要严格干燥除水;以乙腈/水作溶剂的方法毒性小,且可以在室温下进行,缺点是产品收率较低;以四氢呋喃/水作溶剂的方法产品收率较好,易提纯,且无毒性,后处理简单;以对甲苯璜酸酐代替对甲苯璜酰氯的水相合成具有产品收率高,无毒等特点,具有广阔工业化开发前景。同时,本文还对各种方法可能的合成机理做了较为合理的解释。As an intermediate for preparing many cyclodextrin derivatives, 6-O-monotosyl-6-deoxy-β- cyclodextrin（6-O-Ts-β-CD） receives extensive attention. In this paper, the synthetic methods of 6-O-Ts-β-CD are reviewed in order to choose an optimum synthetic route.The method with pyridine as solvent is technically mature and has less byproduct but the production rate is low, the reaction takes longer time, the solvent is toxic and difficult to deal with, in addition the solvent, reagent and the reactors must be dried thoroughly before the reaction. The method with acetonitrile/water as solvents has some advantages such as little toxic, reaction at room temperature, but the production rate is also low. The method with THF/water as solvents is better than the above method and can give a higher production rate. In addition,this method is nearly nontoxic and the solvent is easy to be recycled. The method with p-toluenesulfonic anhydride （Ts2O） substituting p-toluenesulfonyl chloride（p-TsCl） has a high production rate （61% ）, which is hopeful to be the optimum route to synthesize 6- O-Ts-β-CD. The reaction mechanisms of different methods were discussed and a rational explanation was given.

关 键 词：6-OTs-β-环糊精 Β-环糊精 磺酰化 

分 类 号：O636.12[理学—高分子化学]