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 | 182360-86-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 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
• 英文别名: 2-[(1R,4E,7E,10E,13R,15S)-15-methoxy-11-methyl-15-[(E)-3-methyl-5-phenylpent-3-enyl]-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl]acetic acid
• CAS: 182360-86-7
• 化学式: C₃₁H₄₀O₆
• 分子量: 508.655
• InChiKey: UTOPTNNFDWFDLB-ZSTCBBIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以67%的产率得到ripostatin A
  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 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四(三苯基膦)钯 、 偶氮二甲酸二异丙酯 、 戴斯-马丁氧化剂 、 triethylamine tris(hydrogen fluoride) 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 30.41h， 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

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.