【结 构 式】 |
【分子编号】26840 【品名】di[(4aS,8aS)-3-methoxy-11-methyl-6-oxo-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium] 2,3-bis[(2-phenylacetyl)oxy]succinate 【CA登记号】 |
【 分 子 式 】C54H56N2O14 【 分 子 量 】957.04372 【元素组成】C 67.77% H 5.9% N 2.93% O 23.4% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号:(IV)The salification of racemic narwedine (I) with di-p-toluoyl-D-tartaric acid (II) produces high yields of the 1:1 (III) or the 2:1 (IV) salts with a high enantiomeric enhancement (97% and 98% e.e., respectively), a dinamic optical enrichement being produced. In a second step, salts (III) and (IV) are reduced to (-)-galanthamine with L-Selectride, which is finally purified up to >99% e.e. by crystallization of its hydrobromide.
【1】 Chaplin, D.A.; et al.; Dynamic diastereomeric salt resolution of narwedine and its transformation to (-)-galanthamine. Tetrahedron Lett 1998, 39, 37, 6777. |
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) | 26837 | 3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-one | C17H19NO3 | 详情 | 详情 | |
(II) | 26838 | 2,3-bis[(2-phenylacetyl)oxy]succinic acid | C20H18O8 | 详情 | 详情 | |
(III) | 26839 | (4aS,8aS)-3-methoxy-11-methyl-6-oxo-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium 3-carboxy-2,3-bis[(2-phenylacetyl)oxy]propanoate | C37H37NO11 | 详情 | 详情 | |
(IV) | 26840 | di[(4aS,8aS)-3-methoxy-11-methyl-6-oxo-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium] 2,3-bis[(2-phenylacetyl)oxy]succinate | C54H56N2O14 | 详情 | 详情 |
Extended Information