(E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate | 1394247-89-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate
• 英文别名: [(2S,4R,6R)-2-methoxy-6-[(2E)-2-methylhexa-2,5-dienyl]-2-[(E)-3-methyl-5-phenylpent-3-enyl]oxan-4-yl] (2E)-3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]hexa-2,5-dienoate
• CAS: 1394247-89-2
• 化学式: C₃₉H₆₀O₅Si
• 分子量: 636.988
• InChiKey: SBQAEGNHBYSBLM-NVUWALPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.22
• 重原子数：
  45
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 戴斯-马丁氧化剂 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.91h， 生成 2-((1R,4E,7E,10E,13R,15S)-15-methoxy-11-methyl-15-((E)-3-methyl-5-phenylpent-3-en-1-yl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid
  参考文献：
  名称：

  Total Synthesis of Ripostatin A

  摘要：

  The first total synthesis of the bacterial RNA-polymerase inhibitor ripostatin A (1) was achieved. The route utilizes a cyclic methyl acetal intermediate and a sequence of a double Stifle cross-coupling reaction followed by a ring-closing metathesis for the construction of the macrolactone ring. Additionally, an unprecedented formation of the 4-methoxy substituted tetrahydropyrans was observed during the acid catalyzed acetalization of the beta,delta-dihydroxyketone.

  DOI：

  10.1021/ol302219x
• 作为产物：
  描述：

  (Z)-5-(tert-butyldimethylsiloxy)-3-iodo-pent-2-enoic acid 在 四(三苯基膦)钯 、 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.0h， 生成 (E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate
  参考文献：
  名称：

  Total Synthesis of Ripostatin A

  摘要：

  The first total synthesis of the bacterial RNA-polymerase inhibitor ripostatin A (1) was achieved. The route utilizes a cyclic methyl acetal intermediate and a sequence of a double Stifle cross-coupling reaction followed by a ring-closing metathesis for the construction of the macrolactone ring. Additionally, an unprecedented formation of the 4-methoxy substituted tetrahydropyrans was observed during the acid catalyzed acetalization of the beta,delta-dihydroxyketone.

  DOI：

  10.1021/ol302219x

文献信息

• Total Synthesis of Ripostatin A
  作者：Wufeng Tang、Evgeny V. Prusov

  DOI：10.1021/ol302219x

  日期：2012.9.7

  The first total synthesis of the bacterial RNA-polymerase inhibitor ripostatin A (1) was achieved. The route utilizes a cyclic methyl acetal intermediate and a sequence of a double Stifle cross-coupling reaction followed by a ring-closing metathesis for the construction of the macrolactone ring. Additionally, an unprecedented formation of the 4-methoxy substituted tetrahydropyrans was observed during the acid catalyzed acetalization of the beta,delta-dihydroxyketone.