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以生物素、紫杉醇和6-氨基己酸为原料,经酰化、水解、酯化反应等步骤合成具有长臂连接的标题化合物。在三乙胺催化下,生物素与N-羟基琥珀酰亚胺反应生成N-羟基琥珀酰亚胺生物素酯。在氯化亚砜、甲醇反应体系下,由6-氨基己酸合成6-氨基己酸甲酯。在三乙胺作用下,N-羟基琥珀酰亚胺生物素酯和6-氨基己酸甲酯反应生成生物素-氨基己酸甲酯;生物素-氨基己酸甲酯在Li OH·H2O作用下,水解反应得到6-生物素氨基己酸。以DMF为溶剂,在N,N’-二环己基碳二亚胺(DCC)、4-二甲氨基吡啶(DMAP)作用下,6-生物素氨基己酸与紫杉醇反应,生成标题化合物。标题化合物和重要中间体化合物采用IR、1HNMR、MS进行了表征。
Using biotin, paclitaxel and 6-aminocaproic acid as starting materials, the title compounds with long arm linkages were synthesized by acylation, hydrolysis and esterification reactions. Under the catalysis of triethylamine, biotin reacts with N-hydroxysuccinimide to form N-hydroxysuccinimide biotin ester. Methyl 6-aminocaproate was synthesized from 6-aminocaproic acid under thionyl chloride and methanol reaction systems. Under the action of triethylamine, N-hydroxysuccinimide biotin ester reacted with methyl 6-aminocaproate to form biotin-aminocaproic acid methyl ester; the biotin-aminocaproic acid methyl ester reacted with LiOH · H 2 O Under the hydrolysis reaction 6-biotin aminocaproic acid. Reaction of 6-biotin aminocaproic acid with paclitaxel in the presence of N, N’-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) using DMF as a solvent yielded the title compound. The title compounds and important intermediate compounds were characterized by IR, 1H NMR, MS.