methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate | 132628-70-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate
• 英文别名: methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl]benzo[1,2-b;4,3-b']dipyrrole-2-carboxylate
• CAS: 132628-70-7；143314-86-7；149405-53-8；149405-54-9
• 化学式: C₃₃H₃₃N₃O₉
• 分子量: 615.64
• InChiKey: HOSMABYPQXDLGW-FPYOTAMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  148.65
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl (2S*,8S*)-1,2,3,6,7,8-hexahydro-4-hydroxy-8-(methanesulfonyloxy)methyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate
  参考文献：
  名称：

  杜卡霉素的合成研究。2.天然（+）-杜卡霉素A及其三种可能的立体异构体的合成和细胞毒性。

  摘要：

  通过特征在于两种类型的三环中间体的光学拆分和在外消旋化合物的合成中建立的合成方案来实现标题合成。针对P388鼠白血病的体外细胞毒性试验显然表明（+）- 1中环丙烷部分的绝对构型与其细胞毒性密切相关。

  DOI：

  10.1016/s0040-4020(01)86994-5
• 作为产物：
  描述：

  在 盐酸 、 乙酸酐 、 1,8-双二甲氨基萘 、 碳酸氢钠 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.5h， 生成 methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate
  参考文献：
  名称：

  Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer

  摘要：

  The title synthesis was first achieved by employing novel methoxycarbonylation of the C-4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2- carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.

  DOI：

  10.1016/s0040-4020(01)86993-3

文献信息

• First total synthesis of dl-duocarmycin A
  作者：Yasumichi Fukuda、Kazuhiko Nakatani、Yoshio Ito、Shiro Terashima

  DOI：10.1016/s0040-4039(00)97151-x

  日期：1990.1
• Synthetic studies on duocarmycin. 2. Synthesis and cytotoxicity of natural (+)-duocarmycin A and its three possible stereoisomers.
  作者：Yasumichi Fukuda、Kazuhiko Nakatani、Shiro Terashima

  DOI：10.1016/s0040-4020(01)86994-5

  日期：1994.2

  types of the tricyclic intermediates and the synthetic scheme established in the synthesis of racemic compounds. In vitro cytotoxicity assay against P388 murine leukemia obviously showed that the absolute configuration of cyclopropane moiety in (+)-1 is closely related to its cytotoxicity.

  通过特征在于两种类型的三环中间体的光学拆分和在外消旋化合物的合成中建立的合成方案来实现标题合成。针对P388鼠白血病的体外细胞毒性试验显然表明（+）- 1中环丙烷部分的绝对构型与其细胞毒性密切相关。
• Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer
  作者：Yasumichi Fukuda、Yoshio Itoh、Kazuhiko Nakatani、Terashima Shiro

  DOI：10.1016/s0040-4020(01)86993-3

  日期：1994.2

  The title synthesis was first achieved by employing novel methoxycarbonylation of the C-4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2- carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.