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泰利霉素的合成改进 被引量：9

Synthesis of Telithromycin
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摘要 以克拉霉素为原料,经多步反应制得酮内酯类抗生素泰利霉素。环碳酸酯保护2'-O-乙酰基-3-O-脱克拉定糖-6-O-甲基红霉素(3)中的11,12-羟基,用价廉易得的氧化剂如PCC、PDC或NCS等氧化C3-羟基,继用DBU处理可得到酮内酯类抗生素关键中间体2'-O-乙酰基-3-O-脱克拉定糖-6-O-甲基-3-氧代-10,11-脱水红霉素(6)。边链的中间体3-(氨乙酰基)吡啶(10)可由3-乙酰基吡啶经溴化和氨解而得。这两项改进为泰利霉素的合成提供了一条新的实用途径。 A new process for preparation the ketolide antibiotic telithromycin by multistep reactions started from clarithromycin is reported. The key intermediate, 2＇-O-acetyl-3-O-de-cladinose-6-O-methyl-3-oxo-10,11- anhydroerythromycin （6） was obtained by treatment of 2＇-O-acetyl-3-O-de-cladinose-6-O-methyl erythromycin （3） with triphosgene to offord the l l,12-protected compound which was easily oxidated with the cheap reagents such as PCC, PDC or NCS. The oxidated product was reacted with DBU in boiling acetone. A facile preparation of the intermediate 3-（aminoacetyl） pyridine （10）of the side chain from 3-acetylpyridine was via bromination and Sommelet reaction from 3 -acetylpyridine.
作者 尤启冬 魏新 赵英
机构地区 中国药科大学药物化学教研室
出处 《中国医药工业杂志》 CAS CSCD 北大核心 2007年第4期318-320,共3页 Chinese Journal of Pharmaceuticals
关键词 泰利霉素 抗菌剂 酮内酯 克拉霉素 氧化 合成 telithromycin antibacterial ketolide clarithromycin oxidation synthesis
分类号 R978.15 [医药卫生—药品]
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参考文献13

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二级参考文献5

  • 1KASHIMURA M, ASAKA T, MISAWA Y, et al.Synthesis and antibacterial activity of the tricyclic ketolides TE-802 and its analogs[J]. J Antibiot, 2001,54(8):664 - 678.
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中国医药工业杂志
2007年 第4期

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