2'-cyanoethyl-N,N,N',N'-tetraisopropyl phosphoramidite-phosphoramidite | 959467-15-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2'-cyanoethyl-N,N,N',N'-tetraisopropyl phosphoramidite-phosphoramidite
• 英文别名: [2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-N,N-di(propan-2-yl)phosphonamidous acid
• CAS: 959467-15-3
• 化学式: C₁₅H₃₃N₃O₃P₂
• 分子量: 365.393
• InChiKey: YVGOJRQESXMFML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-cyanoethyl-N,N,N',N'-tetraisopropyl phosphoramidite-phosphoramidite 、 N-(9-{5-[tert-butyl-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-phenyl-silanyloxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide 在 三氟乙酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以68%的产率得到
  参考文献：
  名称：

  含氟寡核苷酸的合成与应用

  摘要：

  带有吸附剂叔丁基苯基-1H,1H,2H,2H-七氟癸氧基甲硅烷基 (BPFOS) 基团的核苷亚磷酰胺用于合成含氟标记的寡核苷酸，即。5-mer、10-mer、13-mer、17-mer和19-mer，进行液相萃取。发现标记的低聚物本质上是高度疏水的，在水中沉淀，因此可以很容易地从失败序列中纯化。通过 TBAF 处理使氟硅烷基团脱保护，低聚物很容易通过 CH 3 CN/FC-72 液-液萃取纯化。含氟标记的寡核苷酸具有去除失败序列的高选择性、高回收率（通常为 70-100%）。

  DOI：

  10.1246/cl.2006.1184
• 作为产物：
  描述：

  [N,N-diisopropylchlorophosphoramidite]-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite] 在 水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到2'-cyanoethyl-N,N,N',N'-tetraisopropyl phosphoramidite-phosphoramidite
  参考文献：
  名称：

  Solid-Phase Synthesis of Symmetrical 5‘,5‘-Dinucleoside Mono-, Di-, Tri-, and Tetraphosphodiesters

  摘要：

  [GRAPHICS]Four classes of phosphitylating reagents were subjected to reactions with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound mono-, di-, tri-, and tetraphosphitylating reagents. The solid-phase reagents were reacted with unprotected nucleosides (e.g., thymidine, adenosine, 3'-azido-3'-deoxythymidine, cytidine, or inosine) in the presence of 5-(ethylthio)-1H-tetrazole. Polymerbound nucleosides underwent oxidation with tert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford 5',5'-dinucleoside mono-, di-, tri-, and tetraphosphodiesters in 59-78% yield.

  DOI：

  10.1021/ol7018778

文献信息

• Solid-Phase Synthesis of Symmetrical 5‘,5‘-Dinucleoside Mono-, Di-, Tri-, and Tetraphosphodiesters
  作者：Yousef Ahmadibeni、Keykavous Parang

  DOI：10.1021/ol7018778

  日期：2007.10.1

  [GRAPHICS]Four classes of phosphitylating reagents were subjected to reactions with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound mono-, di-, tri-, and tetraphosphitylating reagents. The solid-phase reagents were reacted with unprotected nucleosides (e.g., thymidine, adenosine, 3'-azido-3'-deoxythymidine, cytidine, or inosine) in the presence of 5-(ethylthio)-1H-tetrazole. Polymerbound nucleosides underwent oxidation with tert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford 5',5'-dinucleoside mono-, di-, tri-, and tetraphosphodiesters in 59-78% yield.
• Synthesis and Application of Fluorous-tagged Oligonucleotides
  作者：Roli Mishra、Satyendra Mishra、Krishna Misra

  DOI：10.1246/cl.2006.1184

  日期：2006.10

  Nucleoside phosphoramidites bearing a adsorbent tert-butylphenyl- 1H,1H,2H,2H-heptafluorodecyloxysilyl (BPFOS) group were used to synthesize fluorous-tagged oligonucleotides, viz. 5-mer, 10-mer, 13-mer, 17-mer, and 19-mer, which were subjected to liquid-phase extraction. The labeled oligomers were found to be highly hydrophobic in nature, become precipitated in water, therefore allowing easy purification

  带有吸附剂叔丁基苯基-1H,1H,2H,2H-七氟癸氧基甲硅烷基 (BPFOS) 基团的核苷亚磷酰胺用于合成含氟标记的寡核苷酸，即。5-mer、10-mer、13-mer、17-mer和19-mer，进行液相萃取。发现标记的低聚物本质上是高度疏水的，在水中沉淀，因此可以很容易地从失败序列中纯化。通过 TBAF 处理使氟硅烷基团脱保护，低聚物很容易通过 CH 3 CN/FC-72 液-液萃取纯化。含氟标记的寡核苷酸具有去除失败序列的高选择性、高回收率（通常为 70-100%）。