[(1S,3E,5S,9S,11S,15R,19R,21S,23E,24S)-11-(4-bromophenyl)-1,15-dihydroxy-19-(hydroxymethyl)-23-(2-methoxy-2-oxoethylidene)-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxatricyclo[19.3.1.15,9]hexacos-3-en-24-yl] octanoate | 913626-18-3

• 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: [(1S,3E,5S,9S,11S,15R,19R,21S,23E,24S)-11-(4-bromophenyl)-1,15-dihydroxy-19-(hydroxymethyl)-23-(2-methoxy-2-oxoethylidene)-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxatricyclo[19.3.1.15,9]hexacos-3-en-24-yl] octanoate
• CAS: 913626-18-3
• 化学式: C₄₁H₅₉BrO₁₃
• 分子量: 839.816
• InChiKey: BCIRUCSWOBNJBR-UFRSTVMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  55
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  177
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(1S,3E,5S,9S,11S,15R,19R,21S,23E,24S)-11-(4-bromophenyl)-1,15-dihydroxy-19-(hydroxymethyl)-23-(2-methoxy-2-oxoethylidene)-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxatricyclo[19.3.1.15,9]hexacos-3-en-24-yl] octanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 50.0~55.0 ℃ 、101.32 kPa 条件下， 反应 4.0h， 以73%的产率得到[(1S,3E,5S,9S,11S,15R,19R,21S,23E,24S)-1,15-dihydroxy-19-(hydroxymethyl)-23-(2-methoxy-2-oxoethylidene)-2,2-dimethyl-17-oxo-11-phenyl-6,12,18,25,26-pentaoxatricyclo[19.3.1.15,9]hexacos-3-en-24-yl] octanoate
  参考文献：
  名称：

  Synthesis and PKC Binding of a New Class of A-Ring Diversifiable Bryostatin Analogues Utilizing a Double Asymmetric Hydrogenation and Cross-Coupling Strategy

  摘要：

  [GRAPHICS]The design, asymmetric synthesis, and biological evaluation of a new class of bryostatin analogues based on a pseudosymmetric spacer domain are described. An aryl bromide diversification site is incorporated allowing access to systematically varied analogues. The new analogues all exhibit potent, nanomolar affinity to PKC.

  DOI：

  10.1021/ol0618149
• 作为产物：
  描述：

  (S)-1-(4-bromophenyl)but-3-en-1-ol 在 二氯二茂钛 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 2,4,6-三氯苯甲酰氯 、 四氯化锡 、 苄基三甲基氢氧化铵 、 三乙基硼氢化锂 、 氟化氢吡啶 、 臭氧 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 46.41h， 生成 [(1S,3E,5S,9S,11S,15R,19R,21S,23E,24S)-11-(4-bromophenyl)-1,15-dihydroxy-19-(hydroxymethyl)-23-(2-methoxy-2-oxoethylidene)-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxatricyclo[19.3.1.15,9]hexacos-3-en-24-yl] octanoate
  参考文献：
  名称：

  Synthesis and PKC Binding of a New Class of A-Ring Diversifiable Bryostatin Analogues Utilizing a Double Asymmetric Hydrogenation and Cross-Coupling Strategy

  摘要：

  [GRAPHICS]The design, asymmetric synthesis, and biological evaluation of a new class of bryostatin analogues based on a pseudosymmetric spacer domain are described. An aryl bromide diversification site is incorporated allowing access to systematically varied analogues. The new analogues all exhibit potent, nanomolar affinity to PKC.

  DOI：

  10.1021/ol0618149

文献信息

• BRYOSTATIN ANALOGUES, SYNTHETIC METHODS AND USES
  申请人：WENDER PAUL A.

  公开号：US20090270492A1

  公开（公告）日：2009-10-29

  Biologically active compounds related to the bryostatin family of compounds, including methods of utilizing the same.

  与拟静脉注射家族相关的生物活性化合物，包括利用这些化合物的方法。
• US8497385B2
  申请人：——

  公开号：US8497385B2

  公开（公告）日：2013-07-30
• Synthesis and PKC Binding of a New Class of A-Ring Diversifiable Bryostatin Analogues Utilizing a Double Asymmetric Hydrogenation and Cross-Coupling Strategy
  作者：Paul A. Wender、Joshua C. Horan

  DOI：10.1021/ol0618149

  日期：2006.9.1

  [GRAPHICS]The design, asymmetric synthesis, and biological evaluation of a new class of bryostatin analogues based on a pseudosymmetric spacer domain are described. An aryl bromide diversification site is incorporated allowing access to systematically varied analogues. The new analogues all exhibit potent, nanomolar affinity to PKC.