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【结 构 式】 
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【分子编号】30668 【品名】benzyl (1S,2R,3S,4S,5R)-5-[[(2S)-4-amino-2-hydroxybutanoyl]amino]-2-[[(2R,3R,6S)-3-[[(benzyloxy)carbonyl]amino]-6-([[(benzyloxy)carbonyl]amino]methyl)tetrahydro-2H-pyran-2-yl]oxy]-4-([(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2,2,2-trifluoroacetyl)amino]tetrahydro-2H-pyran-2-yl]oxy)-3-hydroxycyclohexylcarbamate 【CA登记号】 |
【 分 子 式 】C48H61F3N6O17 【 分 子 量 】1051.0377896 【元素组成】C 54.85% H 5.85% F 5.42% N 8% O 25.88% |
合成路线1
该中间体在本合成路线中的序号：(VII)The acylation of 3,2,6'-tri-N-benzyloxycarbonydibekacin (III) with ethyl trifluoroacetate and K2CO3 gives 3,2',6'-tri-N-benzyloxycarbonyl-3''-trifluoroacetyldibekacin (VI), which is acylated again with (IV) yielding the protected habekacin (VII). Finally, this compound is deprotected by hydrolysis with ammonia in aqueous THF, followed by hydrogenolysis with H2 over Pd/C.
| 【1】 Tsuchiya, T.; Takagi, Y.; Umezawa, S.; 1-N-Acylation of aminocyclitol antibiotics via zinc chelation and regiospecific N-trifluoroacetylation. Tetrahedron Lett 1979, 51, 4951-54. |
| 【2】 Serradell, M.N.; Castaner, J.; Blancafort, P.; Habekacin. Drugs Fut 1983, 8, 5, 410. |
| 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) | 30662 | Dibekacin; 3',4'-Dideoxykanamycin B; (2R,3R,4S,5S,6R)-4-amino-2-[((1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol | C18H37N5O8 | 详情 | 详情 | |
| (II) | 30663 | N-benzyloxycarbonyloxysuccinimide; 1-[[(Benzyloxy)carbonyl]oxy]-2,5-pyrrolidinedione | 13139-17-8 | C12H11NO5 | 详情 | 详情 |
| (III) | 30664 | 3,2,6'-tri-N-benzyloxycarbonydibekacin; Benzyl (1S,2R,3S,4S,5R)-5-amino-4-[[(2R,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]-2-[[(2R,3R,6S)-3-[[(benzyloxy)carbonyl]amino]-6-([[(benzyloxy)carbonyl]amino]methyl)tetrahydro-2H-pyran-2-yl]oxy]-3-hydroxycyclohexylcarbamate | C42H55N5O14 | 详情 | 详情 | |
| (IV) | 30665 | 1-[[(2S)-4-amino-2-hydroxybutanoyl]oxy]-2,5-pyrrolidinedione | C8H12N2O5 | 详情 | 详情 | |
| (VI) | 30667 | 3,2',6'-tri-N-benzyloxycarbonyl-3''-trifluoroacetyldibekacin; Benzyl (1S,2R,3S,4S,5R)-5-amino-2-[[(2R,3R,6S)-3-[[(benzyloxy)carbonyl]amino]-6-([[(benzyloxy)carbonyl]amino]methyl)tetrahydro-2H-pyran-2-yl]oxy]-4-([(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2,2,2-trifluoroacetyl)amino]tetrahydro-2H-pyran-2-yl]oxy)-3-hydroxycyclohexylcarbamate | C44H54F3N5O15 | 详情 | 详情 | |
| (VII) | 30668 | benzyl (1S,2R,3S,4S,5R)-5-[[(2S)-4-amino-2-hydroxybutanoyl]amino]-2-[[(2R,3R,6S)-3-[[(benzyloxy)carbonyl]amino]-6-([[(benzyloxy)carbonyl]amino]methyl)tetrahydro-2H-pyran-2-yl]oxy]-4-([(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2,2,2-trifluoroacetyl)amino]tetrahydro-2H-pyran-2-yl]oxy)-3-hydroxycyclohexylcarbamate | C48H61F3N6O17 | 详情 | 详情 |