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【结 构 式】 
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【分子编号】56893 【品名】(1R,2S)-2-(3-hydroxypropyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium chloride 【CA登记号】 |
【 分 子 式 】C25H36ClNO6 【 分 子 量 】482.01668 【元素组成】C 62.3% H 7.53% Cl 7.36% N 2.91% O 19.92% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of (R)-(-)-5'-methoxylaudanosine (I) with 1,3-dioxa-2-thiane 2,2-dioxide (II) in hot acetone gives the quaternized propylsulfonate (III), which is treated with Ac-Cl in methanol to yield the intermediate isoquinolinium derivative (IV).
| 【1】 Samano, V.; et al.; Synthesis of ultra-short-acting neuromuscular blocker GW 0430: A remarkably stereo- and regioselective synthesis of mixed tetrahydroisquinolinium chlorofumarates. Org Lett 1999, 1, 12, 1993. |
| 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) | 19489 | (1R)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline; 4-[[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl]methyl]-2,6-dimethoxyphenyl methyl ether | C22H29NO5 | 详情 | 详情 | |
| (II) | 56891 | 1,3-propanediol cyclic sulfate;1,3,2-dioxathiane 2,2-dioxide;1,3-Propylene sulfate | 1073-05-8 | C3H6O4S | 详情 | 详情 |
| (III) | 56892 | (1R,2S)-6,7-dimethoxy-2-methyl-2-[3-(sulfonatooxy)propyl]-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium | C25H35NO9S | 详情 | 详情 | |
| (IV) | 56893 | (1R,2S)-2-(3-hydroxypropyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium chloride | C25H36ClNO6 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)The reaction of 2,3-dichlorosuccinic anhydride (VIII) with isoquinolinium intermediate (IV) in dichloromethane gives the dichlorosuccinc acid monoester (IX), which is dehydrochlorinated by means of TEA in dichloromethane to yield the chlorofumaric acid monoester (X). The reaction of (X) with oxalyl chloride in the same solvent affords the acyl chloride (XI), which is finally condensed with the isoquinolinium intermediate (VII) in dichloromethane to provide the target bis isoquinolinium compound.
| 【1】 Samano, V.; et al.; Synthesis of ultra-short-acting neuromuscular blocker GW 0430: A remarkably stereo- and regioselective synthesis of mixed tetrahydroisquinolinium chlorofumarates. Org Lett 1999, 1, 12, 1993. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 56893 | (1R,2S)-2-(3-hydroxypropyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium chloride | C25H36ClNO6 | 详情 | 详情 | |
| (VII) | 56896 | (1S,2R)-2-(3-hydroxypropyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroisoquinolinium chloride | C24H34ClNO6 | 详情 | 详情 | |
| (VIII) | 56897 | (3S,4S)-3,4-dichlorodihydro-2,5-furandione | C4H2Cl2O3 | 详情 | 详情 | |
| (IX) | 56898 | (1R,2S)-2-(3-{[(2R,3R)-3-carboxy-2,3-dichloropropanoyl]oxy}propyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium chloride | C29H38Cl3NO9 | 详情 | 详情 | |
| (X) | 56899 | (1R,2S)-2-(3-{[(Z)-3-carboxy-2-chloro-2-propenoyl]oxy}propyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium chloride | C29H37Cl2NO9 | 详情 | 详情 | |
| (XI) | 56900 | (1R,2S)-2-(3-{[(Z)-2,4-dichloro-4-oxo-2-butenoyl]oxy}propyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium chloride | C29H36Cl3NO8 | 详情 | 详情 |