[(1R,3S,7R,8E,11S,12S,13E,15S,17R,21R,23S)-11,21-dihydroxy-17-(hydroxymethyl)-13-(2-methoxy-2-oxoethylidene)-10,10-dimethyl-5-methylidene-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate | 1028456-08-7

• 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: [(1R,3S,7R,8E,11S,12S,13E,15S,17R,21R,23S)-11,21-dihydroxy-17-(hydroxymethyl)-13-(2-methoxy-2-oxoethylidene)-10,10-dimethyl-5-methylidene-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate
• CAS: 1028456-08-7
• 化学式: C₄₀H₆₂O₁₂
• 分子量: 734.925
• InChiKey: CAVZKWXBKAIQCY-CVKLLBMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  52
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  167
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  [(1R,3S,7R,8E,11S,12S,13E,15S,17R,21R,23S)-17-[[tert-butyl(dimethyl)silyl]oxymethyl]-21-[tert-butyl(diphenyl)silyl]oxy-11-hydroxy-13-(2-methoxy-2-oxoethylidene)-10,10-dimethyl-5-methylidene-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以77%的产率得到[(1R,3S,7R,8E,11S,12S,13E,15S,17R,21R,23S)-11,21-dihydroxy-17-(hydroxymethyl)-13-(2-methoxy-2-oxoethylidene)-10,10-dimethyl-5-methylidene-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.