1D-1-O-<(2-O-arachidonoyl-1-O-stearoyl-sn-glycero)-2-cyanoethyloxyphosphoryl>-2-O-chloroacetyl-3,4,5-tri-O--6-O-levulinoyl-myo-inositol | 204254-04-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 1D-1-O-<(2-O-arachidonoyl-1-O-stearoyl-sn-glycero)-2-cyanoethyloxyphosphoryl>-2-O-chloroacetyl-3,4,5-tri-O--6-O-levulinoyl-myo-inositol
• 英文别名: [(2R)-1-[2-cyanoethoxy-[(1S,2S,3S,4S,5R,6S)-3,4,5-tris[bis(9H-fluoren-9-ylmethoxy)phosphoryloxy]-2-(2-chloroacetyl)oxy-6-(4-oxopentanoyloxy)cyclohexyl]oxyphosphoryl]oxy-3-octadecanoyloxypropan-2-yl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 204254-04-6
• 化学式: C₁₄₁H₁₅₆ClNO₂₅P₄
• 分子量: 2424.13
• InChiKey: REHAASMCPDYRFY-RFWARXEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30.7
• 重原子数：
  172
• 可旋转键数：
  75
• 环数：
  19.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  325
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  1D-1-O-<(2-O-arachidonoyl-1-O-stearoyl-sn-glycero)-2-cyanoethyloxyphosphoryl>-2-O-chloroacetyl-3,4,5-tri-O--6-O-levulinoyl-myo-inositol 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Synthesis of natural PI(3,4,5)P3

  摘要：

  Natural phosphatidylinositol 3,4,5-trisphosphate which has been believed to have stearoyl and arachidonoyl groups at the sn-1 and -2 positions, respectively, has been synthesized using 1,2-O-cyclohexylidene-3,4-O-disiloxanyl-myo-inositol as the pivotal intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00034-3
• 作为产物：
  描述：

  1D-2-O-chloroacetyl-3,4,5-tri-O--6-O-levulinoyl-myo-inositol 、 2-O-arachidonoyl-1-O-stearoyl-sn-glycerol 2-cyanoethyl N,N-diisopropylphosphoramidite 在 四氮唑 、 叔丁基过氧化氢 作用下， 以79%的产率得到1D-1-O-<(2-O-arachidonoyl-1-O-stearoyl-sn-glycero)-2-cyanoethyloxyphosphoryl>-2-O-chloroacetyl-3,4,5-tri-O--6-O-levulinoyl-myo-inositol
  参考文献：
  名称：

  Synthesis of natural PI(3,4,5)P3

  摘要：

  Natural phosphatidylinositol 3,4,5-trisphosphate which has been believed to have stearoyl and arachidonoyl groups at the sn-1 and -2 positions, respectively, has been synthesized using 1,2-O-cyclohexylidene-3,4-O-disiloxanyl-myo-inositol as the pivotal intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00034-3

文献信息

• Synthesis of PI(3,4,5)P3 with unsaturated and saturated fatty acid chains
  作者：Yutaka Watanabe、Mitsunobu Nakatomi

  DOI：10.1016/s0040-4020(99)00551-7

  日期：1999.8

  Synthesis of three PI(3,4,5)P(3)s, sn-1-O-stearoyl-sn-2-O-arachidonoyl, stearoyl-linolenoyl, and distearoyl phosphatidyl-myo-inositol 3,4,5-trisphosphate with the natural configuration for the arachidonoyl version was established by employing 9-fluorenylmethyl-protected phosphate derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.