[(1R,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23S)-11,21-dihydroxy-17-(hydroxymethyl)-5,13-bis(2-methoxy-2-oxoethylidene)-10,10-dimethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate | 1028456-12-3

• 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: [(1R,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23S)-11,21-dihydroxy-17-(hydroxymethyl)-5,13-bis(2-methoxy-2-oxoethylidene)-10,10-dimethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate
• CAS: 1028456-12-3
• 化学式: C₄₂H₆₄O₁₄
• 分子量: 792.962
• InChiKey: KVMNWHUUVCQHCF-USYWVCEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  194
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以2.3 mg的产率得到[(1R,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23S)-11,21-dihydroxy-17-(hydroxymethyl)-5,13-bis(2-methoxy-2-oxoethylidene)-10,10-dimethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate
  参考文献：
  名称：

  Efficient Synthetic Access to a New Family of Highly Potent Bryostatin Analogues via a Prins-Driven Macrocyclization Strategy

  摘要：

  The step-economical synthesis of a new class of bryostatin analogues that contain the complete oxycarbocyclic core ring system of the bryostatin natural products is reported. These agents are convergently assembled via a highly efficient, functional-group-tolerant, and stereoselective Prins-driven macrocyclization. These tetrahydropyranyl B-ring analogues are among our most potent and efficacious analogues to date, exhibiting nanomolar and picomolar activities in protein kinase C affinity assays as well as in cellular antiproliferation assays.

  DOI：

  10.1021/ja8015632

文献信息

• Efficient Synthetic Access to a New Family of Highly Potent Bryostatin Analogues via a Prins-Driven Macrocyclization Strategy
  作者：Paul A. Wender、Brian A. DeChristopher、Adam J. Schrier

  DOI：10.1021/ja8015632

  日期：2008.5.1

  The step-economical synthesis of a new class of bryostatin analogues that contain the complete oxycarbocyclic core ring system of the bryostatin natural products is reported. These agents are convergently assembled via a highly efficient, functional-group-tolerant, and stereoselective Prins-driven macrocyclization. These tetrahydropyranyl B-ring analogues are among our most potent and efficacious analogues to date, exhibiting nanomolar and picomolar activities in protein kinase C affinity assays as well as in cellular antiproliferation assays.