1-[(perfluorooctylpropysulfonylethyl)-(2-cyanoethyl)-phosphate]-2-O-benzyl-sn-glycerol | 1354914-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(perfluorooctylpropysulfonylethyl)-(2-cyanoethyl)-phosphate]-2-O-benzyl-sn-glycerol
• CAS: 1354914-06-9
• 化学式: C₂₆H₂₇F₁₇NO₈PS
• 分子量: 867.515
• InChiKey: HHDJEAUJDIOLTO-NLDXTASESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  54.0
• 可旋转键数：
  24.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  132.15
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-([N,N-diisopropylamino]-2-cyanoethylphosphite)-2-O-benzyl-3-O-(4,4'-dimethoxytrityl)-sn-glycerol 、 1-[(perfluorooctylpropysulfonylethyl)-(2-cyanoethyl)-phosphate]-2-O-benzyl-sn-glycerol 在 4,5-二氰基咪唑 作用下， 以 乙腈 为溶剂， 生成 C₆₀H₆₁F₁₇N₂O₁₄P₂S
  参考文献：
  名称：

  Light fluorous synthesis of glucosylated glycerol teichoic acids

  摘要：

  We here describe the synthesis of glucosylated teichoic acid (TA) fragments using two complementary fluorous scaffolds. The use of a perfluorooctylpropylsulfonylethyl (F-Pse) linker in combination with (glucosyl) glycerol phosphoramidite building blocks allows for the assembly of TA fragments with a terminal phosphate mono-ester, whereas the use of a perfluorooctylsuccinyl spacer delivers TA oligomers featuring a terminal alcohol functionality. These complementary linker systems have been developed because the nature of the TA chain terminus can play a role in the biological activity of the synthetic TAs. A novel alpha-glucosylated glycerolphosphoramidite building block is introduced to allow for a robust light fluorous synthetic protocol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.023
• 作为产物：
  描述：

  在 三乙基硅烷 、 二氯乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 以218 mg的产率得到1-[(perfluorooctylpropysulfonylethyl)-(2-cyanoethyl)-phosphate]-2-O-benzyl-sn-glycerol
  参考文献：
  名称：

  Fluorous Linker Facilitated Synthesis of Teichoic Acid Fragments

  摘要：

  The use of perfluorooctylpropylsulfonylethanol as a new phosphate protecting group and fluorous linker is evaluated in the stepwise solution phase synthesis of a number of biologically relevant (carbohydrate substituted) glycerol teichoic acid fragments. Teichoic acid fragments, up to the dodecamer level, were assembled by means of phosphoramidite chemistry, using a relatively small excess of the building blocks and a repetitive efficient purification procedure of the protected intermediates by fluorous solid phase extraction (F-SPE).

  DOI：

  10.1021/ol2033652