[(2S)-3-[chloro(phenoxy)phosphanyl]oxy-2-octanoyloxypropyl] octanoate | 899827-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S)-3-[chloro(phenoxy)phosphanyl]oxy-2-octanoyloxypropyl] octanoate
• CAS: 899827-23-7
• 化学式: C₂₅H₄₀ClO₆P
• 分子量: 503.016
• InChiKey: LIEKDNLRNXRRSF-SBYCOZGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  33
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S)-3-[chloro(phenoxy)phosphanyl]oxy-2-octanoyloxypropyl] octanoate 在 双氧水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  简化的磷脂酰肌醇（PI），PI3P，PI3,5P 2和脱氧类似物的合成作为潜在的生物探针

  摘要：

  据报道，磷脂酰肌醇（PI），磷脂酰肌醇-3-磷酸酯（PI3P），磷脂酰肌醇-3,5-双磷酸酯（PI3,5P 2）和一系列脱氧形式的高度直接的全合成。进行每个合成以递送光学纯形式的靶标。对于每个合成中的关键步骤是催化不对称磷酸化反应，影响适当的desymmetrization肌醇-肌醇的前体。然后采用通用前体的面向多样性的策略对每种目标化合物进行精细加工。除三种天然产物外，还报道了几种其他简化的脱氧PI类似物的总合成方法。这些合成为这些膜相关信号分子的极性头基/生物靶标相互作用的高精度生物学研究奠定了基础。

  DOI：

  10.1021/jo060702s
• 作为产物：
  描述：

  苯氧基亚磷酰二氯 、 sn-2,3-dioctanoylglycerol 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 [(2S)-3-[chloro(phenoxy)phosphanyl]oxy-2-octanoyloxypropyl] octanoate
  参考文献：
  名称：

  Asymmetric Syntheses of Phosphatidylinositol-3-Phosphates with Saturated and Unsaturated Side Chains through Catalytic Asymmetric Phosphorylation

  摘要：

  Highly direct asymmetric syntheses of phosphatidylinositol-3-phosphate (PI3P) in each enantiomerically pure form have been achieved. The key step involves catalytic asymmetric phosphorylation of meso-myo-inositol derivatives through desymmetrization. Protecting group schemes have been employed that allow for synthesis of PI3P with either saturated or arachidonate side chains, in analogy to the naturally occurring systems. Syntheses in each enantiomeric series are reported that rely on the choice of enantioselective peptide-based catalyst to define the enantiomeric series in which the syntheses are carried out.

  DOI：

  10.1021/ja0466098

文献信息

• Asymmetric Syntheses of Phosphatidylinositol-3-Phosphates with Saturated and Unsaturated Side Chains through Catalytic Asymmetric Phosphorylation
  作者：Bianca R. Sculimbrene、Yingju Xu、Scott J. Miller

  DOI：10.1021/ja0466098

  日期：2004.10.1

  Highly direct asymmetric syntheses of phosphatidylinositol-3-phosphate (PI3P) in each enantiomerically pure form have been achieved. The key step involves catalytic asymmetric phosphorylation of meso-myo-inositol derivatives through desymmetrization. Protecting group schemes have been employed that allow for synthesis of PI3P with either saturated or arachidonate side chains, in analogy to the naturally occurring systems. Syntheses in each enantiomeric series are reported that rely on the choice of enantioselective peptide-based catalyst to define the enantiomeric series in which the syntheses are carried out.
• Streamlined Synthesis of Phosphatidylinositol (PI), PI3P, PI3,5P₂, and Deoxygenated Analogues as Potential Biological Probes
  作者：Yingju Xu、Bianca R. Sculimbrene、Scott J. Miller

  DOI：10.1021/jo060702s

  日期：2006.6.1

  Highly direct total syntheses of phosphatidylinositol (PI), phosphatidylinositol-3-phosphate (PI3P), phosphatidylinositol-3,5-bisphosphate (PI3,5P2), and a range of deoxygenated versions are reported. Each synthesis is carried out to deliver the target in optically pure form. The key step for each synthesis is a catalytic asymmetric phosphorylation reaction that affects desymmetrization of an appropriate

  据报道，磷脂酰肌醇（PI），磷脂酰肌醇-3-磷酸酯（PI3P），磷脂酰肌醇-3,5-双磷酸酯（PI3,5P 2）和一系列脱氧形式的高度直接的全合成。进行每个合成以递送光学纯形式的靶标。对于每个合成中的关键步骤是催化不对称磷酸化反应，影响适当的desymmetrization肌醇-肌醇的前体。然后采用通用前体的面向多样性的策略对每种目标化合物进行精细加工。除三种天然产物外，还报道了几种其他简化的脱氧PI类似物的总合成方法。这些合成为这些膜相关信号分子的极性头基/生物靶标相互作用的高精度生物学研究奠定了基础。