[(2S)-3-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxy-2-octanoyloxypropyl] octanoate | 214068-96-9

• 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: [(2S)-3-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxy-2-octanoyloxypropyl] octanoate
• CAS: 214068-96-9
• 化学式: C₃₂H₅₆NO₆P
• 分子量: 581.773
• InChiKey: STGHOXTZWOBOTM-AYLNDXQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  40
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S)-3-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxy-2-octanoyloxypropyl] octanoate 在 palladium dihydroxide 4,5-二氰基咪唑 、 氢气 、 双氧水 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 甲苯 、 叔丁醇 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：

  [(2R)-3-[(4-methoxyphenyl)methoxy]-2-octanoyloxypropyl] octanoate 在 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 [(2S)-3-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxy-2-octanoyloxypropyl] octanoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives

  摘要：

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.

  DOI：

  10.1021/jo980501r

文献信息

• Preparation of l-α-phosphatidyl-d-myo-inositol 3-phosphate (3-PIP) and 3,5-bisphosphate (3,5-PIP2)
  作者：J.R. Falck、U.Murali Krishna、Jorge H. Capdevila

  DOI：10.1016/s0960-894x(00)00315-2

  日期：2000.8

  Practical, asymmetric total syntheses of the title phospholipids from a readily available myo-inositol derivative as well as short chain and cross-linkable aminoether analogues are described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.
• A synthesis of l-α-phosphatidyl-d-myo-inositol 4,5-bisphosphate (4,5-PIP2) and glyceryl lipid analogs
  作者：J.R. Falck、U.Murali Krishna、Jorge H. Capdevila

  DOI：10.1016/s0040-4039(99)01877-8

  日期：1999.12

  The title bioactive phosphatidylinositide and short-chain glyceryl lipid analogs were prepared from deoxyinosose 2, which was ultimately derived from 3-dehydroshikimic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Concise syntheses of l-α-phosphatidyl-d-myo-inositol 3-phosphate (3-PIP), 5-phosphate (5-PIP), and 3,5-bisphosphate (3,5-PIP2)
  作者：J.R Falck、U.Murali Krishna、Kishta Reddy Katipally、Jorge H Capdevila、Emin T Ulug

  DOI：10.1016/s0040-4039(00)00465-2

  日期：2000.6

  Highly efficient, asymmetric total syntheses of the title phospholipids as well as short chain and crosslinkable aminoether analogs were achieved in five to seven steps from a readily available myo-inositol derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives
  作者：Jian Chen、Li Feng、Glenn D. Prestwich

  DOI：10.1021/jo980501r

  日期：1998.9.1

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.