(S)-(-)-1-O-(1'-(Z)-hexadecenyl)-2-(2-trimethylsilanylethoxymethyl)glycero-3-phosphocholine | 595605-58-6

• 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: (S)-(-)-1-O-(1'-(Z)-hexadecenyl)-2-(2-trimethylsilanylethoxymethyl)glycero-3-phosphocholine
• 英文别名: [(2S)-3-[(Z)-hexadec-1-enoxy]-2-(2-trimethylsilylethoxymethoxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 595605-58-6
• 化学式: C₃₀H₆₄NO₇PSi
• 分子量: 609.9
• InChiKey: MKKNWPURZVBMFS-HYWKDPKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  40
• 可旋转键数：
  29
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  86.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-O-(1'-(Z)-hexadecenyl)-2-(2-trimethylsilanylethoxymethyl)glycero-3-phosphocholine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 18.0h， 生成 (S)-(+)-1-O-(1'-(Z)-hexadecenyl)glycero-3-phosphocholine
  参考文献：
  名称：

  Direct Synthesis of Plasmenylcholine from Allyl-Substituted Glycerols

  摘要：

  We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxyprotected 1-allylglycerol precursors with s-BuLi at -65 to -80degreesC. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.

  DOI：

  10.1021/jo026826w
• 作为产物：
  描述：

  (R)-(+)-1-O-(1'-(Z)-hexadecenyl)-2-(2-trimethylsilanylethoxymethyl)glycerol 在 三乙胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 27.0h， 生成 (S)-(-)-1-O-(1'-(Z)-hexadecenyl)-2-(2-trimethylsilanylethoxymethyl)glycero-3-phosphocholine
  参考文献：
  名称：

  Direct Synthesis of Plasmenylcholine from Allyl-Substituted Glycerols

  摘要：

  We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxyprotected 1-allylglycerol precursors with s-BuLi at -65 to -80degreesC. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.

  DOI：

  10.1021/jo026826w

文献信息

• Direct Synthesis of Plasmenylcholine from Allyl-Substituted Glycerols
  作者：Junhwa Shin、David H. Thompson

  DOI：10.1021/jo026826w

  日期：2003.8.1

  We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxyprotected 1-allylglycerol precursors with s-BuLi at -65 to -80degreesC. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.