((1S,2S,3S,4S,5R,6S)-3-Hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl)-phosphonic acid dimethyl ester | 899426-67-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: ((1S,2S,3S,4S,5R,6S)-3-Hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl)-phosphonic acid dimethyl ester
• CAS: 899426-67-6
• 化学式: C₁₇H₃₅O₁₃P
• 分子量: 478.431
• InChiKey: IGQLPVZTIXWLHT-LTAJLKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  31.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  138.83
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  ((1S,2S,3S,4S,5R,6S)-3-Hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl)-phosphonic acid dimethyl ester 在 四氮唑 、 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
• 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 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到((1S,2S,3S,4S,5R,6S)-3-Hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl)-phosphonic acid dimethyl 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