2,3-bis[(2-phenylacetyl)oxy]succinic acid -Drug Synthesis Database

【结构式】

【分子编号】26838

【品名】2,3-bis[(2-phenylacetyl)oxy]succinic acid

【CA登记号】

【分子式】C₂₀H₁₈O₈

【分子量】386.35812

【元素组成】C 62.18% H 4.7% O 33.13%

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：(II)

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.

参考文献中间体

合成目标

【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	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