Butyric acid (R)-1-butyryloxymethyl-2-{[(1S,2R,3R,4S,5S,6R)-3-(dimethoxy-phosphorylmethoxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-ethyl ester | 899426-68-7

• 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: Butyric acid (R)-1-butyryloxymethyl-2-{[(1S,2R,3R,4S,5S,6R)-3-(dimethoxy-phosphorylmethoxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-ethyl ester
• CAS: 899426-68-7
• 化学式: C₂₉H₅₆O₂₀P₂
• 分子量: 786.699
• InChiKey: LITTUKJORFPQNS-WTTLUXMKSA-N

物化性质

• 沸点：
  739.2±60.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  51.0
• 可旋转键数：
  30.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  215.96
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Butyric acid (R)-1-butyryloxymethyl-2-{[(1S,2R,3R,4S,5S,6R)-3-(dimethoxy-phosphorylmethoxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-ethyl ester 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到Butyric acid (R)-1-butyryloxymethyl-2-[hydroxy-((1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrahydroxy-5-phosphonomethoxy-cyclohexyloxy)-phosphoryloxy]-ethyl ester
  参考文献：
  名称：

  Synthesis and Molecular Recognition of Phosphatidylinositol-3-methylenephosphate

  摘要：

  Phosphatidylinositol-3-phosphate (PtdIns(3)P) is a spatial regulator of vesicular trafficking and other vital cellular processes. We describe the asymmetric total synthesis of a metabolically stabilized analogue, phosphatidylinositol-3-methylenephosphate (PtdIns(3) MP) from a differentially protected myo-inositol. NMR studies of PtdIns(3) MP bound to the N-15-labeled FYVE domain showed significant H-1 and N-15 chemical shift changes relative to the unliganded protein.

  DOI：

  10.1021/ol060903i
• 作为产物：
  描述：

  [(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester 在 四氮唑 、 四丁基氟化铵 、 四丁基高碘酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Butyric acid (R)-1-butyryloxymethyl-2-{[(1S,2R,3R,4S,5S,6R)-3-(dimethoxy-phosphorylmethoxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-ethyl ester
  参考文献：
  名称：

  Synthesis and Molecular Recognition of Phosphatidylinositol-3-methylenephosphate

  摘要：

  Phosphatidylinositol-3-phosphate (PtdIns(3)P) is a spatial regulator of vesicular trafficking and other vital cellular processes. We describe the asymmetric total synthesis of a metabolically stabilized analogue, phosphatidylinositol-3-methylenephosphate (PtdIns(3) MP) from a differentially protected myo-inositol. NMR studies of PtdIns(3) MP bound to the N-15-labeled FYVE domain showed significant H-1 and N-15 chemical shift changes relative to the unliganded protein.

  DOI：

  10.1021/ol060903i