2-cyanoethyl bis-(2-O-(tert-butyldiphenylsilyl)-sn-glycer-1-yl) phosphate | 1187738-15-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-cyanoethyl bis-(2-O-(tert-butyldiphenylsilyl)-sn-glycer-1-yl) phosphate
• 英文别名: 3-[bis[(2S)-2-[tert-butyl(diphenyl)silyl]oxy-3-hydroxypropoxy]-oxidophosphaniumyl]oxypropanenitrile
• CAS: 1187738-15-3
• 化学式: C₄₁H₅₄NO₈PSi₂
• 分子量: 776.026
• InChiKey: AWUWYBJJLKFMTM-PXLJZGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  53
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 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-(2-O-(tert-butyldiphenylsilyl)-sn-glycer-1-yl) phosphate 、 棕榈酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 以82%的产率得到2-cyanoethyl bis-(2-O-(tert-butyldiphenylsilyl)-3-palmitoyl-sn-glycer-1-yl) phosphate
  参考文献：
  名称：

  Modular synthesis of bis(monoacylglycero)phosphate for convenient access to analogues bearing hydrocarbon and perdeuterated acyl chains of varying length

  摘要：

  Bis(monoacylglycero)phosphate is an important phospholipid that controls the structure of late endosomes as well as biological activities that occur there. The study of this lipid is complicated by the fact that acyl migrations are known to generate different regioisomers. Herein, we describe a modular synthesis of 3,3'-BMP derivatives that allows for the incorporation of a range of different acyl chains at a late stage. This approach was exploited to produce eight BMP analogues bearing normal saturated and perdeuterated acyl chains of varying length. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.085
• 作为产物：
  描述：

  2-cyanoethyl bis-(3-O-(4-methoxybenzyl)-2-O-(tertbutyldiphenylsilyl)-sn-glycer-1-yl) phosphate 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到2-cyanoethyl bis-(2-O-(tert-butyldiphenylsilyl)-sn-glycer-1-yl) phosphate
  参考文献：
  名称：

  Modular synthesis of bis(monoacylglycero)phosphate for convenient access to analogues bearing hydrocarbon and perdeuterated acyl chains of varying length

  摘要：

  Bis(monoacylglycero)phosphate is an important phospholipid that controls the structure of late endosomes as well as biological activities that occur there. The study of this lipid is complicated by the fact that acyl migrations are known to generate different regioisomers. Herein, we describe a modular synthesis of 3,3'-BMP derivatives that allows for the incorporation of a range of different acyl chains at a late stage. This approach was exploited to produce eight BMP analogues bearing normal saturated and perdeuterated acyl chains of varying length. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.085

文献信息

• Modular synthesis of bis(monoacylglycero)phosphate for convenient access to analogues bearing hydrocarbon and perdeuterated acyl chains of varying length
  作者：Meng M. Rowland、Michael D. Best

  DOI：10.1016/j.tet.2009.06.085

  日期：2009.8

  Bis(monoacylglycero)phosphate is an important phospholipid that controls the structure of late endosomes as well as biological activities that occur there. The study of this lipid is complicated by the fact that acyl migrations are known to generate different regioisomers. Herein, we describe a modular synthesis of 3,3'-BMP derivatives that allows for the incorporation of a range of different acyl chains at a late stage. This approach was exploited to produce eight BMP analogues bearing normal saturated and perdeuterated acyl chains of varying length. (C) 2009 Elsevier Ltd. All rights reserved.