2-cyanoethyl bis(3-hydroxy-2(S)-O-serachyl-sn-glycer-1-yl)phosphate | 865446-81-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-cyanoethyl bis(3-hydroxy-2(S)-O-serachyl-sn-glycer-1-yl)phosphate
• 英文别名: 3-[bis[(2S)-3-hydroxy-2-[(Z)-octadec-9-enoxy]propoxy]-oxidophosphaniumyl]oxypropanenitrile
• CAS: 865446-81-7
• 化学式: C₄₅H₈₆NO₈P
• 分子量: 800.154
• InChiKey: KFKIXYRWWYQRQV-OQJHDYOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  55
• 可旋转键数：
  45
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl bis(3-hydroxy-2(S)-O-serachyl-sn-glycer-1-yl)phosphate 在 N,O-双(三甲基硅烷基)三氟乙酰胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以84%的产率得到bis(3-hydroxy-2(S)-O-serachyl-sn-glycer-1-yl)phosphate
  参考文献：
  名称：

  Concise Synthesis of Ether Analogues of Lysobisphosphatidic Acid

  摘要：

  We describe a versatile, efficient method for the preparation of ether analogues of (SS)-lysobisphosphatidic acid (LBPA) and its enantiomer from (S)-solketal. Phosphorylation of a protected sn-2-O-octadecenyl glyceryl ether with 2-cyanoethyl bis-N,N-diisopropylamino phosphine and subsequent deprotection generated the bisether LBPA analogues. By simply changing the sequence of deprotection steps, we obtained the (R,R)- and (SS)-enantiomers of 2,2'-bisether LBPA. An ELISA assay with anti-LBPA monoclonal antibodies showed that the bisether LBPAs were recognized with the same affinity as the natural 2,2'-bisoleolyl LBPA.

  DOI：

  10.1021/ol051194w
• 作为产物：
  描述：

  2-cyanoethyl bis(1-O-(p-methoxybenzyl)-2(S)-O-serachyl-sn-glycer-1-yl)phosphate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 以67%的产率得到2-cyanoethyl bis(3-hydroxy-2(S)-O-serachyl-sn-glycer-1-yl)phosphate
  参考文献：
  名称：

  Concise Synthesis of Ether Analogues of Lysobisphosphatidic Acid

  摘要：

  We describe a versatile, efficient method for the preparation of ether analogues of (SS)-lysobisphosphatidic acid (LBPA) and its enantiomer from (S)-solketal. Phosphorylation of a protected sn-2-O-octadecenyl glyceryl ether with 2-cyanoethyl bis-N,N-diisopropylamino phosphine and subsequent deprotection generated the bisether LBPA analogues. By simply changing the sequence of deprotection steps, we obtained the (R,R)- and (SS)-enantiomers of 2,2'-bisether LBPA. An ELISA assay with anti-LBPA monoclonal antibodies showed that the bisether LBPAs were recognized with the same affinity as the natural 2,2'-bisoleolyl LBPA.

  DOI：

  10.1021/ol051194w

文献信息

• Concise Synthesis of Ether Analogues of Lysobisphosphatidic Acid
  作者：Guowei Jiang、Yong Xu、Thomas Falguières、Jean Gruenberg、Glenn D. Prestwich

  DOI：10.1021/ol051194w

  日期：2005.9.1

  We describe a versatile, efficient method for the preparation of ether analogues of (SS)-lysobisphosphatidic acid (LBPA) and its enantiomer from (S)-solketal. Phosphorylation of a protected sn-2-O-octadecenyl glyceryl ether with 2-cyanoethyl bis-N,N-diisopropylamino phosphine and subsequent deprotection generated the bisether LBPA analogues. By simply changing the sequence of deprotection steps, we obtained the (R,R)- and (SS)-enantiomers of 2,2'-bisether LBPA. An ELISA assay with anti-LBPA monoclonal antibodies showed that the bisether LBPAs were recognized with the same affinity as the natural 2,2'-bisoleolyl LBPA.