2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid | 794525-92-1

• 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: 2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid
• 英文别名: (2R,4R,5S)-2-[(4-benzoylphenyl)methyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhexanoic acid
• CAS: 794525-92-1
• 化学式: C₃₇H₄₉NO₆Si
• 分子量: 631.885
• InChiKey: NALRQLULVARZHV-YKILCQELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.08
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid 在 四丁基氟化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 {5-(4-benzoyl-phenyl)-1S-benzyl-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3(1S)-methyl-butylcarbamoyl]-2R-hydroxy-pentyl}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
• 作为产物：
  描述：

  4-溴苯甲酰苯 在 platinum(IV) oxide 咪唑 、 lithium hydroxide 、 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 、 乙二醇二甲醚 、 氯仿 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 58.0h， 生成 2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid
  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.