摘要
目的寻求一种高效、低廉的半合成紫杉醇的途径。方法在可回收非支载型手性配体的催化作用下,通过不对称双羟化反应合成紫杉醇C13侧链,对侧链的羟基和氨基进行保护后生成(4S,5R)-N-苯甲酰基-2-(4′-甲氧基)苯基-4-苯基-1,3-氧氮杂戊环-5-甲酸,进而和7-三乙基硅烷巴卡亭-Ⅲ缩合、去保护获得紫杉醇。结果获得了高光学纯度的紫杉醇C13侧链(化学产率52%,光学纯度99%),紫杉醇的总产率为30%,光学纯度为99%。结论此方法反应步骤少、操作简单、成本低廉,为紫杉醇的半合成开辟了一条新路线。
OBJECTIVE To synthesize the taxol by a new,economical and practical way. METHODS The C13 side chain of the taxol was synthesized via asymmetric dihydroxylation of trans-cinnamate,which was catalyzed by a kind of free recoverable and resued chiral ligand and OsO4, Then the -OH and -NH2 groups of the C13 side chain were protected and （4S,5R）-N-benzoyl-2-（4＇-methoxy） phenyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid was prepared. Finally, the taxol was generated by condensing （4S,5R）-N-benzoyl-2- （ 4＇-methoxy ） phenyl-4-phenyl-1, 3-oxazolidine-5-carboxylicacid with 7-triethysilyl baccatin- Ⅲ, deprotection and purification. RESULTS The C13 side chain of the taxol was obtained with the chemical yield of 52% and e, e. of 99%, Total yield of taxol was 30% ,and e, e. was 99%. CONCLUSION This method to synthesize taxol is so convenient and practical that it is possible to be of economic significance to produce taxol in a large scale.
出处
《中国药学杂志》
CAS
CSCD
北大核心
2007年第9期709-712,共4页
Chinese Pharmaceutical Journal
基金
国家自然科学基金资助项目(50372083)
