2-O-benzyl-1,3-bis[(1,2-di-O-myristoyl-sn-glycero-3)-phosphoryl]glycerol di(2-cyanoethyl) ester | 905911-96-8

• 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: 2-O-benzyl-1,3-bis[(1,2-di-O-myristoyl-sn-glycero-3)-phosphoryl]glycerol di(2-cyanoethyl) ester
• CAS: 905911-96-8
• 化学式: C₇₈H₁₃₈N₂O₁₇P₂
• 分子量: 1437.9
• InChiKey: SUSLLYSZEMEVJE-WFEGAMNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.43
• 重原子数：
  99.0
• 可旋转键数：
  75.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  251.53
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2-O-benzyl-1,3-bis[(1,2-di-O-myristoyl-sn-glycero-3)-phosphoryl]glycerol di(2-cyanoethyl) ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 10.0h， 生成 1,3-bis[(1,2-di-O-myristoyl-sn-glycero-3)-phosphoryl]glycerol diammonium salt
  参考文献：
  名称：

  Synthesis of short and long chain cardiolipins

  摘要：

  A phosphoramidite approach using 2-cyanoethyl N,N-diisopropylchlorophosphoramidite was utilized for the first time to synthesize short chain cardiolipins. The approach was extended to synthesize long chain and their ether analogue. Optically active 1,2-di-O-acylsn-glycerol or 1,2-di-O-myristyl-sn-glycerol was coupled with phosphoramidite reagent and 2-benzyloxy-1,3-propanediol in presence of 1H-tetrazole, followed by in situ oxidation, to give the corresponding protected cardiolipin analogues. The above intermediates were converted into cardiolipin analogues in two steps by deprotection of cyanoethyl and benzyl groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.071
• 作为产物：
  描述：

  1,2-二肉豆蔻酰-sn-甘油 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.25h， 生成 2-O-benzyl-1,3-bis[(1,2-di-O-myristoyl-sn-glycero-3)-phosphoryl]glycerol di(2-cyanoethyl) ester
  参考文献：
  名称：

  Synthesis of short and long chain cardiolipins

  摘要：

  A phosphoramidite approach using 2-cyanoethyl N,N-diisopropylchlorophosphoramidite was utilized for the first time to synthesize short chain cardiolipins. The approach was extended to synthesize long chain and their ether analogue. Optically active 1,2-di-O-acylsn-glycerol or 1,2-di-O-myristyl-sn-glycerol was coupled with phosphoramidite reagent and 2-benzyloxy-1,3-propanediol in presence of 1H-tetrazole, followed by in situ oxidation, to give the corresponding protected cardiolipin analogues. The above intermediates were converted into cardiolipin analogues in two steps by deprotection of cyanoethyl and benzyl groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.071