perfluorooctylpropylsulfonylethanol | 1154463-63-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: perfluorooctylpropylsulfonylethanol
• 英文别名: 2-[3-(perfluorooctyl)propylsulfonyl]ethanol；2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoroundecylsulfonyl)ethanol；2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecylsulfonyl)ethanol
• CAS: 1154463-63-4
• 化学式: C₁₃H₁₁F₁₇O₃S
• 分子量: 570.267
• InChiKey: NHIYENFCDVNHPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  perfluorooctylpropylsulfonylethanol 在 吡啶 、 4,5-二氰基咪唑 、 水 、 碘 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.08h， 生成
  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
• 作为产物：
  描述：

  perfluorooctylpropylsulfidylethanol 在 过氧乙酸 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 2.0h， 以96%的产率得到perfluorooctylpropylsulfonylethanol
  参考文献：
  名称：

  Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry

  摘要：

  The methylsulfonylethoxycarbonyl (Msc) group is presented as a non-lipophilic, base-labile, participating protecting group for carbohydrate alcohols. It can be introduced using Msc-Cl and pyridine and is readily cleaved via beta-elimination under mild basic conditions. Its fluorous counterpart, the perfluorooctyl propyl-sulfonylethoxycarbonyl (FPsc) group, is used in a 'light fluorous' trisaccharide synthesis sequence. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.146

文献信息

• Light fluorous synthesis of glucosylated glycerol teichoic acids
  作者：W.F.J. Hogendorf、A. Kropec、D.V. Filippov、H.S. Overkleeft、J. Huebner、G.A. van der Marel、J.D.C. Codée

  DOI：10.1016/j.carres.2012.02.023

  日期：2012.7

  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.
• Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry
  作者：Asghar Ali、Richard J.B.H.N. van den Berg、Herman S. Overkleeft、Dmitri V. Filippov、Gijsbert A. van der Marel、Jeroen D.C. Codée

  DOI：10.1016/j.tetlet.2009.02.146

  日期：2009.5

  The methylsulfonylethoxycarbonyl (Msc) group is presented as a non-lipophilic, base-labile, participating protecting group for carbohydrate alcohols. It can be introduced using Msc-Cl and pyridine and is readily cleaved via beta-elimination under mild basic conditions. Its fluorous counterpart, the perfluorooctyl propyl-sulfonylethoxycarbonyl (FPsc) group, is used in a 'light fluorous' trisaccharide synthesis sequence. (C) 2009 Elsevier Ltd. All rights reserved.
• Fluorous Linker Facilitated Synthesis of Teichoic Acid Fragments
  作者：Wouter F. J. Hogendorf、Lucien N. Lameijer、Thomas J. M. Beenakker、Herman S. Overkleeft、Dmitri V. Filippov、Jeroen D. C. Codée、Gijsbert A. Van der Marel

  DOI：10.1021/ol2033652

  日期：2012.2.3

  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).