tert-butyl (3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxopentanoate | 1041849-28-8

• 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-5-oxopentanoate
• CAS: 1041849-28-8
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: NAHLHXXNNKHAAT-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxopentanoate 、 (4R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-8-[tert-butyl(diphenyl)silyl]oxy-2-(trimethylsilylmethyl)oct-1-en-4-ol 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以82%的产率得到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
  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：

  在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到tert-butyl (3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxopentanoate
  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.