特利霉素前体化合物的新型合成工艺

Novel Synthesis Route for the Precursor of Telithromycin

摘要: 目的研究特利霉素前体化合物的新合成工艺。方法以3-羟基-6-O-甲基红霉素肟为原料，经乙酰化，氧化，脱肟，10,11-脱水、12-O-咪唑酰基化反应得到特利霉素前体化合物2’-O-乙酰基-3-酮基-10,11-脱水-12-O-咪唑酰基-6-O-甲基红霉素。结果目标物收率为60.8%，经质谱、核磁共振氢谱确证结构。结论新工艺副反应少，原料易得，操作简便。

Abstract: OBJECTIVE To study a new synthetic route of the precursor of telithromycin. METHODS 2’-O-acetate-3- keto-10,11-anhydro-12-O-acylimidazole-6-O-methyl-erythromycin, the precursor of telithromycin, was synthesized from 3-hydroxy-6-O-methyl-erythromycin by acetylation, oxidation, deoximation, followed by 10,11-dehydration and acylation with N-acylimidazole. RESULTS The total yield was up to 60.8%. The chemical structures of target compound were confirmed by 1H-NMR and MS. CONCLUSION The novel synthetic route was facile and characterized by less side-effects.