(2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2-{(S)-1-methoxycarbonyl-2-[1-(2-nitro-benzyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester | 217796-96-8

• 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: (2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2-{(S)-1-methoxycarbonyl-2-[1-(2-nitro-benzyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (2S,3aR,8bR)-2-[[(2S)-1-methoxy-3-[1-[(2-nitrophenyl)methyl]imidazol-4-yl]-1-oxopropan-2-yl]carbamoyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate
• CAS: 217796-96-8
• 化学式: C₄₀H₅₀N₆O₉
• 分子量: 758.872
• InChiKey: VAGHFNXVDIGBOM-KYOWQHJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2-{(S)-1-methoxycarbonyl-2-[1-(2-nitro-benzyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester 在 碘代三甲硅烷 作用下， 反应 1.0h， 以76%的产率得到(S)-2-{[(2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl]-amino}-3-[1-(2-nitro-benzyl)-1H-imidazol-4-yl]-propionic acid methyl ester
  参考文献：
  名称：

  The first total synthesis of roquefortine D

  摘要：

  The synthesis of roquefortine D (1), an alkaloid isolated from the cultures of Penicillium roqueforti, is described. The absolute stereochemistry of the natural product was determined by comparison of its optical rotation with that of the synthetic product. A photo-cleavable o-nitrobenzyl group was utilized for histidine side chain protection, and the cyclisation to the diketopiperazine was carried out under mild conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01957-1
• 作为产物：
  描述：

  在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2-{(S)-1-methoxycarbonyl-2-[1-(2-nitro-benzyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,8-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  The first total synthesis of roquefortine D

  摘要：

  The synthesis of roquefortine D (1), an alkaloid isolated from the cultures of Penicillium roqueforti, is described. The absolute stereochemistry of the natural product was determined by comparison of its optical rotation with that of the synthetic product. A photo-cleavable o-nitrobenzyl group was utilized for histidine side chain protection, and the cyclisation to the diketopiperazine was carried out under mild conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01957-1

文献信息

• The first total synthesis of roquefortine D
  作者：Wei-Chuan Chen、Madeleine M. Joullié

  DOI：10.1016/s0040-4039(98)01957-1

  日期：1998.11

  The synthesis of roquefortine D (1), an alkaloid isolated from the cultures of Penicillium roqueforti, is described. The absolute stereochemistry of the natural product was determined by comparison of its optical rotation with that of the synthetic product. A photo-cleavable o-nitrobenzyl group was utilized for histidine side chain protection, and the cyclisation to the diketopiperazine was carried out under mild conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.