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【结 构 式】 
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【药物名称】OPT-11 【化学名称】1-O,1'-O-(Butane-1,4-diyl)bis(methylimino)bis[1(S)-hydroxyethylene]bis(oxy)bis[4(R),6(S)-diamino-3(S)-hydroxycyclohexan-2(R),1(R)-diyl]bis(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranose) 【CA登记号】 【 分 子 式 】C34H72N10O14 【 分 子 量 】845.01154 |
【开发单位】Optimer Pharmaceuticals (Originator) 【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Aminoglycosides |
合成路线1
The protected azidoglycoside derivative (I) is condensed with (R)-glycidol tosylate (II) to produce the glycidyl ether (III). Epoxide opening in (III) with N,N'-dimethyl-1,4-butanediamine (IV) furnishes the diamine-linked bis azidoglycoside (V). The title compound is then obtained by simultaneous reduction of the azido groups and O benzyl groups cleavage in (V) upon catalytic hydrogenation over Pearlman's catalyst.
| 【1】 Liang, C.; Duffield, J.J.; Marby, K.A.; Rabuka, D.; Romero, A.; Sgarbi, P.W.M.; Shue, Y.-K.; Sucheck, J.; Yao, S.; Zhang, Z.; Cheng, M.; Chan, F.K.; Hu, C.; Ng, S.P.; Hwang, S.-B.; The synthesis and biological activity of multivalent aminoglycoside analogues of OPT-11. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1687. |
| 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) | 62185 | (1R,2R,3S,5R,6S)-3,5-diazido-2-{[(2S,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-yl]oxy}-6-(benzyloxy)cyclohexanol | C33H36N12O6 | 详情 | 详情 | |
| (II) | 16242 | (2R)oxiranylmethyl 4-methylbenzenesulfonate; (2R)-(-)-Glycidyl tosylate | 113826-06-5 | C10H12O4S | 详情 | 详情 |
| (III) | 62187 | (2R,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)-2-({(1R,2R,3S,4R,6S)-4,6-diazido-3-(benzyloxy)-2-[(2R)oxiranylmethoxy]cyclohexyl}oxy)tetrahydro-2H-pyran; (2R,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-5-(benzyloxy)-2-({(1R,2R,3S,4R,6S)-4,6-diazido-3-(benzyloxy)-2-[(2R)oxiranylmethoxy]cyclohexyl}oxy)tetrahydro-2H-pyran-4-yl benzyl ether | C36H40N12O7 | 详情 | 详情 | |
| (IV) | 62188 | N-methyl-N-[4-(methylamino)butyl]amine; N~1~,N~4~-dimethyl-1,4-butanediamine | C6H16N2 | 详情 | 详情 | |
| (V) | 62189 | (1S)-2-{[(1R,2R,3S,5R,6S)-3,5-diazido-2-{[(2R,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-yl]oxy}-6-(benzyloxy)cyclohexyl]oxy}-1-[{4-[((1S)-2-{[(1R,2R,3S,5R,6S)-3,5-diazido-2-{[(2R,3R,4R,5S,6R)-3-azido-6-(azidomethyl | C76H92N26O14 | 详情 | 详情 |