methyl (8S)-8-(chloromethyl)-5-formyl-4-hydroxy-2-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】42107

【品名】methyl (8S)-8-(chloromethyl)-5-formyl-4-hydroxy-2-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate

【CA登记号】

【分子式】C₁₅H₁₅ClN₂O₄

【分子量】322.74788

【元素组成】C 55.82% H 4.68% Cl 10.98% N 8.68% O 19.83%

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：(III)

The segment-A moiety of duocarmycin analogue (I) was formylated with dichloromethyl methyl ether in the presence of TiCl4 to produce aldehyde (II). Opening of the cyclopropane ring of (II) by means of HCl in EtOAc gave rise to chloromethyl compound (III), which was subsequently coupled with 4-methoxycinnamic acid (IV) by means of EDC to furnish the title amide.

参考文献中间体

合成目标

【1】 Okamoto, A.; Okabe, M.; Saito, H.; Amishiro, N.; Synthesis and antitumor activity of duocarmycin derivatives: Modification at the C-7 position of segement-A of A-ring pyrrole compounds. Bioorg Med Chem 2000, 8, 5, 1195.

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)	38365	methyl (3bR,4aS)-2-methyl-8-oxo-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate		C₁₄H₁₄N₂O₃	详情	详情
(II)	42106	methyl (3bR,4aS)-7-formyl-2-methyl-8-oxo-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate		C₁₅H₁₄N₂O₄	详情	详情
(III)	42107	methyl (8S)-8-(chloromethyl)-5-formyl-4-hydroxy-2-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate		C₁₅H₁₅ClN₂O₄	详情	详情
(IV)	42108	(E)-3-(4-methoxyphenyl)-2-propenoic acid	830-09-1	C₁₀H₁₀O₃	详情	详情

Extended Information