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【结 构 式】 
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【药物名称】EP-1579 【化学名称】4"-Acetyl-6-O-methyl-11-O-[5-(4-phenyl-1H-imidazol-1- yl)-2-pentenyl]erythromycin A 【CA登记号】 【 分 子 式 】C54H85N3O14 【 分 子 量 】1000.29125 |
【开发单位】Enanta Pharmaceuticals (Originator) 【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Macrolides |
合成路线1
Alkylation of clarithromycin diacetate (I) with allyl t-butyl carbonate (II) in the presence of palladium catalyst affords the 11-O-allyl ether (III). Subsequent metathesis reaction between ally ether (III) and 1-butenyl-4-phenylimidazole (IV) employing Grubb's catalyst provides adduct (V). Finally, methanolysis of the 2'-acetate ester of (V) gives rise to the target compound.
| 【1】 Niu, D.; Phan, L.T.; Haley, T.; Polemeropoulos, A.; Or, Y.; Syntheses and antibacterial activities of novel 11-O-substituted macrolide and ketolide derivatives. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1666. |
| 【2】 Or, Y.S.; Phan, L.T.; Niu, D. (Enanta Pharmaceuticals, Inc.); 11-O-Substd. macrolides and their descladinose derivs.. US 2003114396; US 6673774; WO 0347600 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 53089 | (2S,3S,4R,6R)-6-[((3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecanyl)oxy]-4-methoxy-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate | n/a | C42H73NO15 | 详情 | 详情 |
| (II) | 62295 | allyl tert-butyl carbonate | C8H14O3 | 详情 | 详情 | |
| (III) | 62680 | (2S,3S,4R,6R)-6-{[(3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-12-(allyloxy)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecanyl]oxy}-4- | C45H77NO15 | 详情 | 详情 | |
| (IV) | 62681 | 1-(3-butenyl)-4-phenyl-1H-imidazole | C13H14N2 | 详情 | 详情 | |
| (V) | 62682 | (2S,3S,4R,6R)-6-[((3R,4S,5R,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-12-{[(E)-5-(4-phenyl-1H-imidazol-1-yl)-2- | C56H87N3O15 | 详情 | 详情 |
Extended Information