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 | 1041849-34-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 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
• CAS: 1041849-34-6
• 化学式: C₄₅H₇₈O₇Si₃
• 分子量: 815.367
• InChiKey: NJLCXBNMNRUZJB-LYBWPPJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.15
• 重原子数：
  55
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-4-((2S,6R)-6-((S)-2-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butyl)-4-methylenetetrahydro-2H-pyran-2-yl)butanoate 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.52h， 以92%的产率得到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
  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

文献信息

• The Design, Synthesis, and Evaluation of C7 Diversified Bryostatin Analogs Reveals a Hot Spot for PKC Affinity
  作者：Paul A. Wender、Vishal A. Verma

  DOI：10.1021/ol801235h

  日期：2008.8.7

  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.