tert-butyl N-[(2S)-1-[(2R,3aR,8bR)-4-acetyl-2-[(4-methoxyphenyl)carbamoyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate | 1257632-05-5

• 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: tert-butyl N-[(2S)-1-[(2R,3aR,8bR)-4-acetyl-2-[(4-methoxyphenyl)carbamoyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
• CAS: 1257632-05-5
• 化学式: C₄₁H₄₇N₅O₆
• 分子量: 705.854
• InChiKey: AEFZSFZAOOOLNU-FGYKHKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  52
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[(2R,3aR,8bR)-4-acetyl-2-[(4-methoxyphenyl)carbamoyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3aR,8bR)-4-acetyl-3-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]-N-(4-methoxyphenyl)-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2-carboxamide
  参考文献：
  名称：

  First total synthesis and stereochemical revision of okaramine M

  摘要：

  We describe the first total synthesis of the reported and revised structures of okaramine M (1 and 7) through the Ugi three-component reaction of pyrroloindole imine 10 with p-methoxyphenyl isonitrile and N-Boc-L-tryptophan, followed by cyclization and epimerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.026
• 作为产物：
  描述：

  (3aR,8aR)-8-acetyl-3a-(2-methylbut-3-en-2-yl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole 、 4-甲氧基苯异腈 、 N-tert-butyloxycarbonyl-tryptophanal 以 甲苯 为溶剂， 以78%的产率得到tert-butyl N-[(2S)-1-[(2R,3aR,8bR)-4-acetyl-2-[(4-methoxyphenyl)carbamoyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  First total synthesis and stereochemical revision of okaramine M

  摘要：

  We describe the first total synthesis of the reported and revised structures of okaramine M (1 and 7) through the Ugi three-component reaction of pyrroloindole imine 10 with p-methoxyphenyl isonitrile and N-Boc-L-tryptophan, followed by cyclization and epimerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.026

文献信息

• First total synthesis and stereochemical revision of okaramine M
  作者：Toshimasa Iizuka、Satoshi Takiguchi、Yuh-suke Kumakura、Naoki Tsukioka、Kazuhiro Higuchi、Tomomi Kawasaki

  DOI：10.1016/j.tetlet.2010.09.026

  日期：2010.11

  We describe the first total synthesis of the reported and revised structures of okaramine M (1 and 7) through the Ugi three-component reaction of pyrroloindole imine 10 with p-methoxyphenyl isonitrile and N-Boc-L-tryptophan, followed by cyclization and epimerization. (C) 2010 Elsevier Ltd. All rights reserved.