2,6-Bis-O-<(benzyloxy)methyl>-3,4,5-tris-O-(dibenzylphosphoryl)-D-myo-inositol | 163563-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-Bis-O-<(benzyloxy)methyl>-3,4,5-tris-O-(dibenzylphosphoryl)-D-myo-inositol
• 英文别名: 2,6-O-bis(benzyloxymethyl)-D-myo-insitol 3,4,5-tris(dibenzyl phosphate)
• CAS: 163563-70-0
• 化学式: C₆₄H₆₇O₁₇P₃
• 分子量: 1201.15
• InChiKey: BKDNKXPLFYJCLZ-OIKZZOOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.26
• 重原子数：
  84.0
• 可旋转键数：
  34.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  191.43
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  1,2-Di-O-octanoyl-sn-glycerol benzyl (N,N-diisopropylamino)phosphoramidite 、 2,6-Bis-O-<(benzyloxy)methyl>-3,4,5-tris-O-(dibenzylphosphoryl)-D-myo-inositol 在 四氮唑 、 间氯过氧苯甲酸 作用下， 生成 2,6-Di-O-<(benzyloxy)methyl>-3,4,5-tris-O-(dibenzylphosphoryl)-D-myo-inositol 1-O-(1,2-di-O-octanoyl-sn-glycerol benzyl phosphate)
  参考文献：
  名称：

  Intracellular Mediators: Synthesis of L-.alpha.-Phosphatidyl-D-myo-inositol 3,4,5-Trisphosphate and Glyceryl Ether Analogs

  摘要：

  L-alpha-Phosphatidyl-D-myo-inositol 3,4,5-trisphosphate (3,4,5-PIP3), the mot prominent member of a new class of intracellular second messengers, and two ether analogs were conveniently prepared from the differentially functionalized D-myo-inositol intermediate 7 which was ultimately derived from the unique cyclitol precursor dehydroshikimic acid(1). Critical transformations included the stereoselective hydride reduction of the shikimate ketone, exclusive osmylation from the a-face to give 3, controlled enolization of 4, and dioxirane epoxidation with in situ rearrangement affording ketone 5. Dioctanoyl 3,4,5-PIP3 (9a) and its dioctyl ether analog Sb;selectively activated the delta, epsilon, and eta-isotypes of protein kinase C (PKC).

  DOI：

  10.1021/jo00116a023
• 作为产物：
  描述：

  1-O-(4-Methoxybenzyl)-2,6-bis-O-<(benzyloxy)methyl>-3,4,5-tris-O-(dibenzylphosphoryl)-D-myo-inositol 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以92%的产率得到2,6-Bis-O-<(benzyloxy)methyl>-3,4,5-tris-O-(dibenzylphosphoryl)-D-myo-inositol
  参考文献：
  名称：

  Intracellular Mediators: Synthesis of L-.alpha.-Phosphatidyl-D-myo-inositol 3,4,5-Trisphosphate and Glyceryl Ether Analogs

  摘要：

  L-alpha-Phosphatidyl-D-myo-inositol 3,4,5-trisphosphate (3,4,5-PIP3), the mot prominent member of a new class of intracellular second messengers, and two ether analogs were conveniently prepared from the differentially functionalized D-myo-inositol intermediate 7 which was ultimately derived from the unique cyclitol precursor dehydroshikimic acid(1). Critical transformations included the stereoselective hydride reduction of the shikimate ketone, exclusive osmylation from the a-face to give 3, controlled enolization of 4, and dioxirane epoxidation with in situ rearrangement affording ketone 5. Dioctanoyl 3,4,5-PIP3 (9a) and its dioctyl ether analog Sb;selectively activated the delta, epsilon, and eta-isotypes of protein kinase C (PKC).

  DOI：

  10.1021/jo00116a023

文献信息

• Synthesis of Modular Headgroup Conjugates Corresponding to All Seven Phosphatidylinositol Polyphosphate Isomers for Convenient Probe Generation
  作者：Denghuang Gong、Heidi E. Bostic、Matthew D. Smith、Michael D. Best

  DOI：10.1002/ejoc.200900476

  日期：2009.8

  derivatized analogs of use for different studies. In addition to the application of this strategy to generate PI-(4,5)-P2 headgroup probes, we also report the synthesis of PIPn–amine conjugates corresponding to all seven naturally existing isomers. This approach will be invaluable for generating the range of probe structures that is required to elucidate the intricacies of PIPn signaling. (© Wiley-VCH Verlag

  磷脂酰肌醇聚磷酸脂 (PIPns) 在重要的生物学途径中发挥着关键作用，这些分子的信号活动缺陷与许多疾病状态有关。因此，有必要了解这些脂质在生物途径中的复杂作用，这通常涉及它们作为位点特异性配体的作用，将受体募集到细胞膜表面。然而，PIPn 家族成员的复杂结构，其中存在七种生物活性异构体，使研究复杂化。PIPn 结构的衍生类似物可用作阐明信号和结合活性的化学工具。在此处，我们提出了一种有效的方法来探测 PIPn 头基的氨基缀合物可以在合成的最后一步方便地功能化的生成，以获得用于不同研究的许多衍生类似物。除了应用此策略生成 PI-(4,5)-P2 头基探针外，我们还报告了与所有七种天然存在的异构体相对应的 PIPn-胺缀合物的合成。这种方法对于生成阐明 PIPn 信号的复杂性所需的探针结构范围非常宝贵。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim