(R)-3-((tert-butyldimethylsilyl)oxy)-4-((2S,4R,6R)-6-((S)-2-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butyl)-4-((methoxycarbonyl)oxy)tetrahydro-2H-pyran-2-yl)butanoic acid | 1041849-69-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-3-((tert-butyldimethylsilyl)oxy)-4-((2S,4R,6R)-6-((S)-2-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butyl)-4-((methoxycarbonyl)oxy)tetrahydro-2H-pyran-2-yl)butanoic acid
• CAS: 1041849-69-7
• 化学式: C₄₃H₇₂O₉Si₃
• 分子量: 817.296
• InChiKey: UTVDEKFXRIRXOB-YQYWCZHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.69
• 重原子数：
  55.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-3-((tert-butyldimethylsilyl)oxy)-4-((2S,4R,6R)-6-((S)-2-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butyl)-4-((methoxycarbonyl)oxy)tetrahydro-2H-pyran-2-yl)butanoic acid 、 2,4,6-三氯苯甲酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of C7 Diversified Bryostatin Analogs Reveals a Hot Spot for PKC Affinity

  摘要：

  The first series of systematically varied C7-functionalized bryostatin analogs (12 members in all) have been synthesized through an efficient and convergent route. A new hotspot for PKC affinity, not present in the natural products, has been discovered, allowing for affinity control and potentially for selective regulation of PKC isozymes. Several analogs exhibit single-digit nanomolar affinity to PKC and display superior activity compared to bryostatin against the leukemia cell line K562.

  DOI：

  10.1021/ol801235h
• 作为产物：
  描述：

  tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-4-((2S,4R,6R)-6-((S)-2-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butyl)-4-((methoxycarbonyl)oxy)tetrahydro-2H-pyran-2-yl)butanoate 在 2,6-二甲基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 水 、 potassium carbonate 、 sodium hydrogensulfate monohydrate 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 29.58h， 以3.0 mg的产率得到(R)-3-((tert-butyldimethylsilyl)oxy)-4-((2S,4R,6R)-6-((S)-2-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butyl)-4-((methoxycarbonyl)oxy)tetrahydro-2H-pyran-2-yl)butanoic acid
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of C7 Diversified Bryostatin Analogs Reveals a Hot Spot for PKC Affinity

  摘要：

  The first series of systematically varied C7-functionalized bryostatin analogs (12 members in all) have been synthesized through an efficient and convergent route. A new hotspot for PKC affinity, not present in the natural products, has been discovered, allowing for affinity control and potentially for selective regulation of PKC isozymes. Several analogs exhibit single-digit nanomolar affinity to PKC and display superior activity compared to bryostatin against the leukemia cell line K562.

  DOI：

  10.1021/ol801235h