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【结 构 式】 
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【分子编号】57013 【品名】(1aS,2S,7bS)-2-(dimethoxymethyl)-2-methyl-6-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromene; [(1aS,2S,7bS)-2-methyl-6-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromen-2-yl](methoxy)methyl methyl ether 【CA登记号】 |
【 分 子 式 】C13H15NO6 【 分 子 量 】281.26524 【元素组成】C 55.51% H 5.38% N 4.98% O 34.13% |
合成路线1
该中间体在本合成路线中的序号：(II)The asymmetric epoxidation of (R)-2-methyl-6-nitro-2H-1-benzopyran-2-carbaldehyde (I) with NaOCl catalyzed by the chiral catalyst Mn(III)-Salen gives the chiral epoxide (II), which is opened by means of NH3 in hot ethanol to yield the amino alcohol (III). The reaction of (III) with diphenylcyanocarbonimidate (IV) by means of TEA in DMF/isopropanol affords the N-cyano-O-phenylisourea (V), which by reaction with benzylamine (VI) in the same solvent provides the N-cyanoguanidine (VII). Finally, the nitro group of this compound is reduced with H2 over Pd/C or NaBH4 in methanol to give the target amino derivative.
| 【1】 Lee, S.; Yoo, S.; Yi, K.Y.; et al.; A novel anti-ischemic ATP-sensitive potassium channel (KATP) opener without vasorelaxation: N-(6-aminobenzopyranyl)-N-benzyl-N'-cyanoguanidine analogue. J Med Chem 2001, 44, 24, 4207. |
| 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) | 51836 | (2S)-2-(dimethoxymethyl)-2-methyl-6-nitro-2H-chromene; methoxy[(2S)-2-methyl-6-nitro-2H-chromen-2-yl]methyl methyl ether | C13H15NO5 | 详情 | 详情 | |
| (II) | 57013 | (1aS,2S,7bS)-2-(dimethoxymethyl)-2-methyl-6-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromene; [(1aS,2S,7bS)-2-methyl-6-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromen-2-yl](methoxy)methyl methyl ether | C13H15NO6 | 详情 | 详情 | |
| (III) | 51838 | (2S,3S,4R)-4-amino-2-(dimethoxymethyl)-2-methyl-6-nitro-3,4-dihydro-2H-chromen-3-ol | C13H18N2O6 | 详情 | 详情 | |
| (IV) | 25868 | 1-[(cyanoimino)(phenoxy)methoxy]benzene | 107-37-9 | C14H10N2O2 | 详情 | 详情 |
| (V) | 57014 | (2S,3S,4R)-4-{[(cyanoimino)(phenoxy)methyl]amino}-2-(dimethoxymethyl)-3-hydroxy-2-methyl-6-nitro-3,4-dihydro-2H-chromene | C21H22N4O7 | 详情 | 详情 | |
| (VI) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
| (VII) | 51841 | N-benzyl-N''-cyano-N'-[(2S,3S,4R)-2-(dimethoxymethyl)-3-hydroxy-2-methyl-6-nitro-3,4-dihydro-2H-chromen-4-yl]guanidine | C22H25N5O6 | 详情 | 详情 |