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以肉桂酸为原料,通过单过氧化硫酸氢钾复盐(Oxone)进行环氧化反应,再用溴苄保护,制得3-苯基缩水甘油酸苄酯,然后经Ritter反应,形成口恶唑环的结构,再脱去酯基保护基、酸化,得到4,5-二氢-2,4-二苯基-1,3-口恶唑-5-甲酸,后者再经过拆分即得到紫杉醇C-13侧链前体。将7-三乙基硅氧基巴卡亭Ⅲ与该C-13侧链前体对接,然后脱三乙基硅烷(TES)保护基,酸化开环,即得紫杉醇,总收率为4.5%。部分中间体和目标产物的结构经1HNMR、13CNMR、MS进行了表征。
Using cinnamic acid as raw material, epoxidation reaction was carried out by oxone mono-peroxymonosulfate and then benzyl bromide to prepare benzyl 3-phenylglycidyl ester, which was then subjected to Ritter reaction The structure of the oxazole ring, then deprotected ester protecting group, acidification, to give 4,5-dihydro-2,4-diphenyl-1,3-oxazole-5-carboxylic acid, which is then split Paclitaxel C-13 side chain precursor was obtained. The 7-triethylsiloxy baccatin III was docked with the C-13 side chain precursor, and then triethylsilane (TES) protection group was deprotected, and the ring was opened to give paclitaxel in a total yield of 4.5% . The structures of some intermediates and target products were characterized by 1HNMR, 13CNMR and MS.