(R)-(-)-3-氯-1,2-丙二醇合成(S)-(+)-缩水甘油对甲苯磺酸酯的研究

Synthesis of (S)-(+)-glycidyl tosylate from (R)-(-)-3-chloro-1,2-propanediol

以环氧氯丙烷动力学水解制备(S)-环氧氯丙烷过程中所产生的水解副产物为原料合成医药中间体(S)-(+)-缩水甘油对甲苯磺酸酯。环氧氯丙烷动力学水解制备(S)-环氧氯丙烷过程中所产生的水解副产物经过精密分馏得到(R)-(-)-3-氯-1,2-丙二醇,然后经脱HCl环化得到(S)-(+)-缩水甘油,再进一步与对甲苯磺酰氯反应得到(S)-(+)-缩水甘油对甲苯磺酸酯。在适宜合成条件下其得率为73%。

（S） - （ ＋ ）-glycidyl tosylate, an important medicinal intermediate, is synthesized from （ R ）- （ - ） -3- chloro- 1,2- propanediol,which is one of the side products produced in the process of preparing （S）-（ ＋ ）-epichlorohydrin by hydrolytic kinetic resolution of （ ± ）-epichlorohydrin. The side product obtained from the kinetic resolution of racemic （ ＋ ）- epichlorohydrin is finely fractionated to cut a fraction of （R）-（ - ）-3-chloro-1,2-propanediol, and it is further cyclized into （S）-（ ＋ ）-glycidol under the basic condition. （ S）-（ ＋ ）-glycidyl tosylate is obtained by esterifying （ S）-（ ＋ ）-glycidol with p-toluenesulfonyl chloride. Under optimal conditions the yield of product can reach 73%.