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【结 构 式】 
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【分子编号】39511 【品名】(2R,3R,4R,5R)-2-[((1S,2R,3R,4S,6R)-4,6-diamino-3-[[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol 【CA登记号】 |
【 分 子 式 】C19H39N5O7 【 分 子 量 】449.54816 【元素组成】C 50.76% H 8.74% N 15.58% O 24.91% |
合成路线1
该中间体在本合成路线中的序号：(I)1) By methylation of gentamicin C1a (I) with methyl p-toluenesulfonate (A) in acetonitrile. 2) By methylation of gentamicin C1a (I) with methyl bromide (B) in methanol. 3) The reaction of gentamicin C1a (I) with CS2 in ethanol gives the 6'-N-dithiocarbamylgentamicin (II), C1a which is reduced with LiAlH4 in refluxing THF.
| 【1】 Castaner, J.; Sweetman, A.J.; Serradell, M.N.; Blancafort, P.; Sagamicin. Drugs Fut 1979, 4, 5, 360. |
| 【2】 Matsushima, H.; et al.; JP 75123640 . |
| 【3】 Matsushima, H.; et al.; JP 75129531 . |
| 【4】 Matsushima, H.; et al.; JP 75126639 . |
| 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) | 23403 | Methyl p-toluenesulfonate; Methyl 4-methylbenzenesulfonate; Methyl 4-toluenesulfonate | 80-48-8 | C8H10O3S | 详情 | 详情 |
| (I) | 39511 | (2R,3R,4R,5R)-2-[((1S,2R,3R,4S,6R)-4,6-diamino-3-[[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol | C19H39N5O7 | 详情 | 详情 | |
| (II) | 39512 | [(2S,5R,6R)-5-amino-6-[((1R,2R,3S,4R,6S)-4,6-diamino-3-[[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl)oxy]tetrahydro-2H-pyran-2-yl]methylcarbamodithioic acid | C20H39N5O7S2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)4) The reaction of gentamicin C1a (I) with formaldehyde in ethanol gives 6'-N-methylenegentamicin C1a (III), which is then reduced with NaBH4, or with hot formic acid. 5) The reaction of gentamicin C1a (I) with ethyl chloroformate (C) by means of NaOH in dioxane yields ethyl 6'-carbamategentamicin C1a (IV), which is then reduced with LiAlH4 in THF.
| 【1】 Matsushima, H.; et al.; JP 75149647 . |
| 【2】 Matsushima, H.; et al.; JP 75149646 . |
| 【3】 Castaner, J.; Sweetman, A.J.; Serradell, M.N.; Blancafort, P.; Sagamicin. Drugs Fut 1979, 4, 5, 360. |
| 【4】 Matsushima, H.; et al.; JP 75131949 . |
| 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) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
| (I) | 39511 | (2R,3R,4R,5R)-2-[((1S,2R,3R,4S,6R)-4,6-diamino-3-[[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol | C19H39N5O7 | 详情 | 详情 | |
| (III) | 39513 | (2R,3R,4R,5R)-2-[[(1S,2R,3R,4S,6R)-4,6-diamino-3-([(2R,3R,6S)-3-amino-6-[(methyleneamino)methyl]tetrahydro-2H-pyran-2-yl]oxy)-2-hydroxycyclohexyl]oxy]-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol | C20H39N5O7 | 详情 | 详情 | |
| (IV) | 39514 | ethyl [(2S,5R,6R)-5-amino-6-[((1R,2R,3S,4R,6S)-4,6-diamino-3-[[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl)oxy]tetrahydro-2H-pyran-2-yl]methylcarbamate | C22H43N5O9 | 详情 | 详情 |