hexadecanoic acid {(1R,2R)-1-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxymethyl]-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-hexanoyloxy}-propyl ester | 607358-68-9

• 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: hexadecanoic acid {(1R,2R)-1-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxymethyl]-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-hexanoyloxy}-propyl ester
• 英文别名: [(2R,3R)-1-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxy-3-hexadecanoyloxy-4-[phenylmethoxy-[2-(phenylmethoxycarbonylamino)ethoxy]phosphoryl]oxybutan-2-yl] hexadecanoate
• CAS: 607358-68-9
• 化学式: C₆₆H₁₀₈N₂O₁₂P₂
• 分子量: 1183.54
• InChiKey: YODDKAYVWPCCKV-LLCTVMNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.9
• 重原子数：
  82
• 可旋转键数：
  55
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Phosphoric acid dibenzyl ester (1R,2R,3S,4S,5R,6S)-3-benzyloxy-4,6-bis-benzyloxymethoxy-2-(bis-benzyloxy-phosphoryloxy)-5-hydroxy-cyclohexyl ester 、 hexadecanoic acid {(1R,2R)-1-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxymethyl]-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-hexanoyloxy}-propyl ester 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)

  摘要：

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.

  DOI：

  10.1021/jo011185a
• 作为产物：
  描述：

  2-苄氧羰基氨基-1-乙醇 在 四氮唑 、 盐酸 、 4-二甲氨基吡啶 、 水 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 hexadecanoic acid {(1R,2R)-1-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxymethyl]-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-hexanoyloxy}-propyl ester
  参考文献：
  名称：

  Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)

  摘要：

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.

  DOI：

  10.1021/jo011185a

文献信息

• Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)
  作者：Piotr W. Rzepecki、Glenn D. Prestwich

  DOI：10.1021/jo011185a

  日期：2002.8.1

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.