2′-O-乙酰基-3-酮基-10,11-脱水-12-O-咪唑酰基-6-O-甲基红霉素的合成

Synthesis of 2′-O-acetate-3-keto-10,11-anhydro-12-O-acylimidazole-6-O-methylerythromycin

以2′-O-乙酰基-3-羟基-11,12-环碳酸酯-6-O-甲基红霉素为原料,通过DMSO/P2O5氧化其3-羟基;再以六甲基二硅胺基钠为碱,经消除、咪唑酰基化"一锅煮"方法合成了抗生素泰利霉素的关键中间体——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,总收率68.3%。

The key intermediate of preparing telithromycin,2′-O-acetate-3-keto-10,11-anhydro-12-O-acylimidazole-6-O-methylerythromycin,was synthesized from 2′-O-acetate-3-hydroxy-11,12-carbonate-6-O-methylerythromycin by oxidation of the 3-hydroxyl with DMSO/P2O5,followed by one-pot method of elimination reaction and acylation with N-acylimidazole in the presence of sodium bis（trimethylsilyl）amide.The total yield was 68.3%.