1,5-O-bis(t-butyldimethylsilyl)-3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol | 797038-11-0

• 英文名称: 1,5-O-bis(t-butyldimethylsilyl)-3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol
• CAS: 797038-11-0
• 化学式: C₅₃H₇₁O₉PSi₂
• 分子量: 939.286
• InChiKey: VXWUASVPQAPIFG-PMMVLBEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.46
• 重原子数：
  65.0
• 可旋转键数：
  21.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,5-O-bis(t-butyldimethylsilyl)-3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol 在 四氮唑 、 双氧水 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 38.0h， 生成 Octanoic acid (R)-2-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,4,6-tris-benzyloxy-3-(bis-benzyloxy-phosphoryloxy)-5-hydroxy-cyclohexyloxy]-phosphoryloxy}-1-octanoyloxymethyl-ethyl ester
  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
• 作为产物：
  描述：

  (+)-2,4,6-tri-O-benzyl-myo-inositol-3-phosphate 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 1,5-O-bis(t-butyldimethylsilyl)-3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol
  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

• Catalyst-dependent syntheses of phosphatidylinositol-5-phosphate–DiC8 and its enantiomer
  作者：Katherine J. Kayser-Bricker、Peter A. Jordan、Scott J. Miller

  DOI：10.1016/j.tet.2008.03.037

  日期：2008.7

  Peptide-based catalysts have been applied to the enantioselective syntheses of the title Compounds, with this being the first report of the synthesis of an ent-PI5P analogue. The key steps in the synthesis involve asymmetric phosphorylation catalysis. Additional maneuvers were developed with a protecting groups scheme that enabled efficient, streamlined syntheses of these important mediators of biochemical events. (C) 2008 Elsevier Ltd. All rights reserved.