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【结 构 式】 
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【药物名称】A-174982 【化学名称】6-Deoxy-6-(2-propynyloxy)erythromycin A 【CA登记号】198482-62-1 【 分 子 式 】C40H69NO13 【 分 子 量 】771.99483 |
【开发单位】Abbott (Originator) 【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Macrolides |
合成路线1
Alkylation of protected erythromycin (I) at the 6-hydroxyl group with propargyl bromide provided ether (II). Hydrolysis of the cyclohexylidene ketal group of (II) with concomitant desilylation with AcOH gave (III). The oxime function of (III) was then hydrolyzed using either sodium bisulfite and formic acid or sodium nitrite and HCl to afford the title ketone.
| 【1】 Bui, M.H.; Plattner, J.J.; Ramney, p.M.; Nilius, A.M.; Chu, D.T.W.; Or, Y.S.; Wang, S.; Clark, R.F.; Henry, R.F.; Ma, Z.; Novel 6-O-substituted erythromycin A derivatives. Synthesis and antibacterial activity. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-125. |
| 【2】 Or, Y.S.; Chu, D.T.; Clark, R.F.; Ma, Z. (Abbott Laboratories Inc.); 6-O-Substd. erythromycins and method for making them. EP 0918783; EP 1007530; JP 2000509712; US 6075011; WO 9742204; WO 9742206 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 11176 | 3-Bromopropyne; 3-Bromo-1-propyne | 106-96-7 | C3H3Br | 详情 | 详情 |
| (I) | 28388 | (3R,4S,5R,6R,7S,9R,11S,12R,13S,14R)-6-([(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-[(trimethylsilyl)methyl]tetrahydro-2H-pyran-2-yl]oxy)-14-ethyl-7,12,13-trihydroxy-4-([(2R,4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)methyl]tetrahydro-2H-pyran-2-yl]oxy)-3,5,7,9,11,13-hexamethyl-2,10-oxacyclotetradecanedione 10-[O-(1-isopropoxycyclohexyl)oxime] | C54H104N2O12Si2 | 详情 | 详情 | |
| (II) | 28394 | (3R,4S,5R,6R,7S,9R,11S,12R,13S,14R)-6-([(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-[(trimethylsilyl)methyl]tetrahydro-2H-pyran-2-yl]oxy)-14-ethyl-12,13-dihydroxy-4-([(2R,4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)methyl]tetrahydro-2H-pyran-2-yl]oxy)-3,5,7,9,11,13-hexamethyl-7-(2-propynyloxy)-2,10-oxacyclotetradecanedione 10-[O-(1-isopropoxycyclohexyl)oxime] | C57H106N2O12Si2 | 详情 | 详情 | |
| (III) | 28395 | (3R,4S,5R,6R,7S,9R,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-12,13-dihydroxy-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyl-7-(2-propynyloxy)-2,10-oxacyclotetradecanedione 10-oxime | C40H70N2O13 | 详情 | 详情 |
Extended Information