用一种可回收的配体催化合成紫杉醇C_(13)片段  

Synthesis of taxol side chain precursor with a new recoverable ligand

作　　者：金瑛[1] 孙晓莉[1] 陈惠[1] 张生勇[1] 陈雷[1] 

机构地区：[1]第四军医大学基础部化学教研室,陕西西安710033

出　　处：《第四军医大学学报》2004年第7期610-612,共3页Journal of the Fourth Military Medical University

基　　金：国家自然科学基金 (2 0 2 72 0 82 )

摘　　要：目的 :建立一种经济的方法合成紫杉醇C1 3 侧链(2R ,3S) 3 苯甲酰胺基 2 羟基 3 苯基丙酸异丙酯 2 .方法 :以反式肉桂酸异丙酯为原料 ,N 溴代苯甲酰胺为助氧化供氮试剂 ,在配体 4存在下进行锇催化的不对称氨羟化反应 ,可以得到很高光学产率的抗癌药物紫杉醇的C1 3 片段 2 .当反应结束后 ,向体系加入少量乙醚 ,过滤 ,就可使配体 4得到回收 .结果 :C1 3 片段 2化学产率 39% ,对映体过量 98% .配体回收率76 % .结论 :这种合成方法成本低 ,操作简便 .特别是配体容易合成 。AIM: To develop a simple and economical method to achieve taxol side chain precursor, (2R,3S) isoproplyl 3 benzamido 2 hydroxy 3 phenylpropionate. METHODS: A highly enantioselective C 13 side chain 2 was obtained by osmium catalyzed asymmetric aminohydroxylation (AA) of isopropyl trans cinnamate, with N bromobenzamide as an oxidant /nitrogen reagent in the presence of ligand 4. After reaction, diethyl ether was added and filtered and ligand was recovered. RESULTS: Total yield of C 13 side chain 2 was 39%, the enantiomeric excess was 98% and recovery rate of ligand 4 was 76%. CONCLUSION: This synthetic process is simple and economical, for the ligand, better than polymer surpported ligand, can be easily prepared, recovered and reused.

关 键 词：配体 紫杉醇C13 片段 

分 类 号：O621[理学—有机化学]