5(S)-tert-butoxycarbonylamino-4(R)-(tert-butyldimethylsilanyloxy)-6-phenyl-2-(4-(2-phenyl-1,3-dioxolan-2-yl)-benzyl)hexanoic acid | 794525-87-4

• 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: 5(S)-tert-butoxycarbonylamino-4(R)-(tert-butyldimethylsilanyloxy)-6-phenyl-2-(4-(2-phenyl-1,3-dioxolan-2-yl)-benzyl)hexanoic acid
• 英文别名: (2R,4R,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenyl-2-[[4-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl]hexanoic acid
• CAS: 794525-87-4
• 化学式: C₃₉H₅₃NO₇Si
• 分子量: 675.938
• InChiKey: GTXBKXHRSHKVJM-SAUDROSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5(S)-tert-butoxycarbonylamino-4(R)-(tert-butyldimethylsilanyloxy)-6-phenyl-2-(4-(2-phenyl-1,3-dioxolan-2-yl)-benzyl)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 {1S-benzyl-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-2R-hydroxy-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-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：

  1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯 在 platinum(IV) oxide 咪唑 、 lithium hydroxide 、 氢气 、 sodium ethanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.0h， 生成 5(S)-tert-butoxycarbonylamino-4(R)-(tert-butyldimethylsilanyloxy)-6-phenyl-2-(4-(2-phenyl-1,3-dioxolan-2-yl)-benzyl)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.