7-{(S)-2-[(S)-3-Carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionylamino}-heptanoic acid allyl ester | 182171-96-6

• 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: 7-{(S)-2-[(S)-3-Carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionylamino}-heptanoic acid allyl ester
• 英文别名: (3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-[[(2S)-1-oxo-1-[(7-oxo-7-prop-2-enoxyheptyl)amino]propan-2-yl]amino]butanoic acid
• CAS: 182171-96-6
• 化学式: C₃₂H₃₉N₃O₈
• 分子量: 593.677
• InChiKey: QOXJVISXXYFLFY-IDISGSTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  43
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  、 7-{(S)-2-[(S)-3-Carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionylamino}-heptanoic acid allyl ester 生成
  参考文献：
  名称：

  The first synthesis of a tricyclic homodetic peptide employing coordinated orthogonal protection

  摘要：

  In an effort to cause significant conformational distortion and thereby possibly generate a pure SRIF antagonist, we undertook the synthesis of 2, the first homodetic tricyclic peptide. This required five dimensional orthogonal amino protection and three carboxyl protecting groups to allow the selective closure of the three rings and to differentiate the epsilon-amino groups of the two lysines. We also exploited acid catalyzed removal from the resin to achieve selective deprotection of a side chain carboxyl moiety simultaneously with its partner amino group for subsequent cyclization. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)01221-x
• 作为产物：
  描述：

  7-氨基庚酸 在 氯化亚砜 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 7-{(S)-2-[(S)-3-Carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionylamino}-heptanoic acid allyl ester
  参考文献：
  名称：

  第一三环同源肽的合成。使用协调的正交脱保护实现定向环闭合

  摘要：

  发现一种或多种受体亚型的生长抑素拮抗剂仍然是一个重要的目标。因此，我们进行了同源三环肽（1）的合成，希望引起构象畸变，从而实现这一生物学目标。合成策略要求五维正交氨基保护。选择羧基和氨基保护基以确保所需的选择性闭环。还选择氨基保护基以允许两个赖氨酸ε-氨基之间的区分。实现了改进的通用环化程序，其以93％的收率提供了复杂的c-八肽13。还显示了1的生物测定结果。

  DOI：

  10.1016/s0040-4020(98)00354-8

文献信息

• Synthesis of the first tricyclic homodetic peptide. Use of coordinated orthogonal deprotection to achieve directed ring closure
  作者：Ralph Hirschmann、Wenqing Yao、Byron Arison、Laurie Maechler、Avery Rosegay、Paul A. Sprengeler、Amos B. Smith

  DOI：10.1016/s0040-4020(98)00354-8

  日期：1998.6

  important goal. We therefore undertook the synthesis of the homodetic tricyclic peptide (1) hoping to cause conformational distortion and thereby achieve this biological goal. The synthetic strategy called for five dimensional orthogonal amino protection. The carboxyl and amino protecting groups were selected to assure the desired selective ring closures. The amino protecting groups were also chosen

  发现一种或多种受体亚型的生长抑素拮抗剂仍然是一个重要的目标。因此，我们进行了同源三环肽（1）的合成，希望引起构象畸变，从而实现这一生物学目标。合成策略要求五维正交氨基保护。选择羧基和氨基保护基以确保所需的选择性闭环。还选择氨基保护基以允许两个赖氨酸ε-氨基之间的区分。实现了改进的通用环化程序，其以93％的收率提供了复杂的c-八肽13。还显示了1的生物测定结果。
• The first synthesis of a tricyclic homodetic peptide employing coordinated orthogonal protection
  作者：Ralph Hirschmann、Wenqing Yao、Byron Arison、Laurie Maechler、Avery Rosegay、Paul A Sprengeler、Amos B Smith

  DOI：10.1016/0040-4039(96)01221-x

  日期：1996.8

  In an effort to cause significant conformational distortion and thereby possibly generate a pure SRIF antagonist, we undertook the synthesis of 2, the first homodetic tricyclic peptide. This required five dimensional orthogonal amino protection and three carboxyl protecting groups to allow the selective closure of the three rings and to differentiate the epsilon-amino groups of the two lysines. We also exploited acid catalyzed removal from the resin to achieve selective deprotection of a side chain carboxyl moiety simultaneously with its partner amino group for subsequent cyclization. Copyright (C) 1996 Elsevier Science Ltd