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 | 1041849-70-0

• 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: 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
• CAS: 1041849-70-0
• 化学式: C₄₇H₈₀O₉Si₃
• 分子量: 873.403
• InChiKey: LXNLYGHRIZIQQB-NREVGYPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.95
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  tert-butyl (3R)-3-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,4R,6R)-6-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-4-[tert-butyl(diphenyl)silyl]oxybutyl]-4-hydroxyoxan-2-yl]butanoate 、 氯甲酸甲酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 以5.1 mg的产率得到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
  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