Phosphoric acid benzyl ester (R)-2-methoxy-3-octadecyloxy-propyl ester (1R,2R,3S,4R,6R)-2,3,4-tris-benzyloxy-6-methoxy-cyclohexyl ester | 498554-92-0

• 英文名称: Phosphoric acid benzyl ester (R)-2-methoxy-3-octadecyloxy-propyl ester (1R,2R,3S,4R,6R)-2,3,4-tris-benzyloxy-6-methoxy-cyclohexyl ester
• CAS: 498554-92-0
• 化学式: C₅₇H₈₃O₁₀P
• 分子量: 959.254
• InChiKey: XUELOFMGZZBGGQ-XUTREXIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.18
• 重原子数：
  68.0
• 可旋转键数：
  38.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  100.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid benzyl ester (R)-2-methoxy-3-octadecyloxy-propyl ester (1R,2R,3S,4R,6R)-2,3,4-tris-benzyloxy-6-methoxy-cyclohexyl ester 在 20percent Pd(OH)2/C 氢气 作用下， 以 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以96%的产率得到SH-5
  参考文献：
  名称：

  Novel PI Analogues Selectively Block Activation of the Pro-survival Serine/Threonine Kinase Akt

  摘要：

  The synthesis from l-quebrachitol of a series of 3-deoxygenated ether lipid-type phosphatidylinositol (PI) analogues is reported, that selectively block activation of Akt and downstream substrates without affecting activation of the upstream kinase, PDK-1, or other kinases downstream of ras such as MAPK in H157 and H1703 lung cancer cells that have high levels of constitutively active Akt. The 2-hydroxyl in these compounds was deleted or alkylated with the intent to preclude metabolic degradation of these compounds by PI-specific phospholipase C (PI-PLC). PI analogues with phosphate linkers are more effective than those with carbonate linkers. Specific inhibition of Akt by these compounds validates ligand design targeted to the PH domains of crucial signaling proteins, thus providing a unique class of possible cancer therapeutics.

  DOI：

  10.1021/ja0285159
• 作为产物：
  描述：

  联萘二苯磷 在 四氮唑 、 ammonium cerium(IV) nitrate 、 sodium hydride 、 二正丁基氧化锡 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 3.33h， 生成 Phosphoric acid benzyl ester (R)-2-methoxy-3-octadecyloxy-propyl ester (1R,2R,3S,4R,6R)-2,3,4-tris-benzyloxy-6-methoxy-cyclohexyl ester
  参考文献：
  名称：

  Novel PI Analogues Selectively Block Activation of the Pro-survival Serine/Threonine Kinase Akt

  摘要：

  The synthesis from l-quebrachitol of a series of 3-deoxygenated ether lipid-type phosphatidylinositol (PI) analogues is reported, that selectively block activation of Akt and downstream substrates without affecting activation of the upstream kinase, PDK-1, or other kinases downstream of ras such as MAPK in H157 and H1703 lung cancer cells that have high levels of constitutively active Akt. The 2-hydroxyl in these compounds was deleted or alkylated with the intent to preclude metabolic degradation of these compounds by PI-specific phospholipase C (PI-PLC). PI analogues with phosphate linkers are more effective than those with carbonate linkers. Specific inhibition of Akt by these compounds validates ligand design targeted to the PH domains of crucial signaling proteins, thus providing a unique class of possible cancer therapeutics.

  DOI：

  10.1021/ja0285159