Progress in Synthesis of 6-OTs-��-Cyclodextrin

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Abstract As an intermediate for preparing many cyclodextrin derivatives,6-O-monotosyl6-deoxy-��-cyclodextrin(6-O-Ts-��-CD) receives extensive attention.In this paper,the synthetic methods of 6-O-Ts-��-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(Ts_2O) 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-��-CD.The reaction mechanisms of different methods were discussed and a rational explanation was given.

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Received 2006-11-15; published 2006-11-15

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ZHANG Yi-min,LIU Chun-yang,WANG Xue-gong,WAN Xian-kai,WANG Yi-wei.Progress in Synthesis of 6-OTs-��-Cyclodextrin[J] Chemcial Industry and Engineering, 2006,V23(6): 539-543

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