(1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester | 794525-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S)-1-[(2R,4R)-4-[(4-benzoylphenyl)methyl]-5-oxooxolan-2-yl]-2-phenylethyl]carbamate
• CAS: 794525-91-0
• 化学式: C₃₁H₃₃NO₅
• 分子量: 499.607
• InChiKey: JICXZDMVBLLMSH-KWXIBIRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester 在 咪唑 、 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 tert-butyl N-[(2S,3R,5R)-6-[[(2S)-1-[[(2S)-1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentylamino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-[(4-benzoylphenyl)methyl]-3-[tert-butyl(dimethyl)silyl]oxy-6-oxo-1-phenylhexan-2-yl]carbamate
  参考文献：
  名称：

  Stereoselective Synthesis of Photoreactive Peptidomimetic γ-Secretase Inhibitors

  摘要：

  The first asymmetric synthesis of novel, potent photoreactive gamma-secretase inhibitors 2 and 3 has been accomplished. Two stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO2-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing gamma-secretase activity in the plasma membrane of intact cells.

  DOI：

  10.1021/jo0486948
• 作为产物：
  描述：

  4-溴苯甲酰苯 在 platinum(IV) oxide 正丁基锂 、 氢气 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 51.0h， 生成 (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Photoreactive Peptidomimetic γ-Secretase Inhibitors

  摘要：

  The first asymmetric synthesis of novel, potent photoreactive gamma-secretase inhibitors 2 and 3 has been accomplished. Two stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO2-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing gamma-secretase activity in the plasma membrane of intact cells.

  DOI：

  10.1021/jo0486948

文献信息

• Stereoselective Synthesis of Photoreactive Peptidomimetic γ-Secretase Inhibitors
  作者：Jiong Chun、Ye Ingrid Yin、Guangli Yang、Leonid Tarassishin、Yue-Ming Li

  DOI：10.1021/jo0486948

  日期：2004.10.1

  The first asymmetric synthesis of novel, potent photoreactive gamma-secretase inhibitors 2 and 3 has been accomplished. Two stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO2-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing gamma-secretase activity in the plasma membrane of intact cells.