(9S,10R,13S,14S)-9-((tert-butoxycarbonyl)amino)-2,2,10,14-tetramethyl-8,12-dioxo-5,7,11-trioxa-2-silahexadecan-13-yl (R)-4-(((S)-2-(benzyloxy)propanoyl)oxy)-2,2-dimethyl-3-oxo-5-phenylpentanoate | 1554478-28-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (9S,10R,13S,14S)-9-((tert-butoxycarbonyl)amino)-2,2,10,14-tetramethyl-8,12-dioxo-5,7,11-trioxa-2-silahexadecan-13-yl (R)-4-(((S)-2-(benzyloxy)propanoyl)oxy)-2,2-dimethyl-3-oxo-5-phenylpentanoate
• CAS: 1554478-28-2
• 化学式: C₄₄H₆₅NO₁₃Si
• 分子量: 844.085
• InChiKey: KTUILORJHSFAII-WUDKTLFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  59.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  179.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (9S,10R,13S,14S)-9-((tert-butoxycarbonyl)amino)-2,2,10,14-tetramethyl-8,12-dioxo-5,7,11-trioxa-2-silahexadecan-13-yl (R)-4-(((S)-2-(benzyloxy)propanoyl)oxy)-2,2-dimethyl-3-oxo-5-phenylpentanoate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以96%的产率得到(2S,3R)-3-[(2S,3S)-2-[(4R)-4-[(2S)-2-hydroxypropanoyl]oxy-2,2-dimethyl-3-oxo-5-phenylpentanoyl]oxy-3-methylpentanoyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
  参考文献：
  名称：

  First total synthesis of prunustatin A

  摘要：

  In this study, we achieved the first total synthesis of natural prunustatin A (1), a novel inhibitor of glucose-regulated protein 78 (GRP78) expression. A key feature included a 15-membered ring macrocyclization, which was successfully accomplished by employing Shiina macrolactonization using 2-methyl-6-nitrobenzoic anhydride (MNBA) and 4-dimethylaminopyridine (DMAP). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.106
• 作为产物：
  描述：

  在 吡啶 、 草酰氯 、 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (9S,10R,13S,14S)-9-((tert-butoxycarbonyl)amino)-2,2,10,14-tetramethyl-8,12-dioxo-5,7,11-trioxa-2-silahexadecan-13-yl (R)-4-(((S)-2-(benzyloxy)propanoyl)oxy)-2,2-dimethyl-3-oxo-5-phenylpentanoate
  参考文献：
  名称：

  First total synthesis of prunustatin A

  摘要：

  In this study, we achieved the first total synthesis of natural prunustatin A (1), a novel inhibitor of glucose-regulated protein 78 (GRP78) expression. A key feature included a 15-membered ring macrocyclization, which was successfully accomplished by employing Shiina macrolactonization using 2-methyl-6-nitrobenzoic anhydride (MNBA) and 4-dimethylaminopyridine (DMAP). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.106