(-)-(3S,4aS,8aS,2'S,3'S)-2-[3'-amino-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide | 1014685-58-5

• 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: (-)-(3S,4aS,8aS,2'S,3'S)-2-[3'-amino-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide
• 英文别名: (3S,4aS,8aS)-2-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide
• CAS: 1014685-58-5
• 化学式: C₂₄H₃₉N₃O₂
• 分子量: 401.593
• InChiKey: YJRJYYPXNAHNMD-WIYBCGNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  78.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(3S,4aS,8aS,2'S,3'S)-2-[3'-amino-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide 、 N-(2-喹啉基羰基)-L-天冬氨酰胺 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以88%的产率得到Butanediamide, N1-[(1S,2S)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-, (2S)-
  参考文献：
  名称：

  Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir

  摘要：

  A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidomimetics with various residues. Finally the total synthesis of two diastereoisomer analogues of HIV-Protease inhibitor Saquinavir has been achieved and their biological activity evaluated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.020
• 作为产物：
  描述：

  (-)-(3S,4aS,8aS,2'S,3'S)-2-[3'-azido-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (-)-(3S,4aS,8aS,2'S,3'S)-2-[3'-amino-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir

  摘要：

  A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidomimetics with various residues. Finally the total synthesis of two diastereoisomer analogues of HIV-Protease inhibitor Saquinavir has been achieved and their biological activity evaluated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.020

文献信息

• Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir
  作者：Giuliana Righi、Simona Ciambrone、Carlo Bonini、Pietro Campaner

  DOI：10.1016/j.bmc.2007.10.020

  日期：2008.1

  A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidomimetics with various residues. Finally the total synthesis of two diastereoisomer analogues of HIV-Protease inhibitor Saquinavir has been achieved and their biological activity evaluated. (C) 2007 Elsevier Ltd. All rights reserved.