O-[O-[N,N-diisopropylchlorophosphoramidite]-2-cyanoethylphosphite]-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]-2-cyanoethylphosphite | 929217-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: O-[O-[N,N-diisopropylchlorophosphoramidite]-2-cyanoethylphosphite]-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]-2-cyanoethylphosphite
• 英文别名: [Chloro-[di(propan-2-yl)amino]phosphanyl] [2-cyanoethoxy-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyphosphanyl] 2-cyanoethyl phosphite；[chloro-[di(propan-2-yl)amino]phosphanyl] [2-cyanoethoxy-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyphosphanyl] 2-cyanoethyl phosphite
• CAS: 929217-13-0
• 化学式: C₂₁H₄₀ClN₅O₆P₄
• 分子量: 617.927
• InChiKey: AZONDCCXNRMJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-[O-[N,N-diisopropylchlorophosphoramidite]-2-cyanoethylphosphite]-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]-2-cyanoethylphosphite 在 水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到[2-cyanoethoxy-[2-cyanoethoxy-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyphosphanyl]oxyphosphanyl]oxy-N,N-di(propan-2-yl)phosphonamidous acid
  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
• 作为产物：
  描述：

  [2-Cyanoethoxy-[di(propan-2-yl)amino]phosphanyl] [2-cyanoethoxy(hydroxy)phosphanyl] 2-cyanoethyl phosphite 、 二氯-N,N-二异丙基亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 生成 O-[O-[N,N-diisopropylchlorophosphoramidite]-2-cyanoethylphosphite]-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]-2-cyanoethylphosphite
  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

• MODIFIED OLIGONUCLEOTIDES CONTAINING DIPHOSPHODIESTER INTERNUCLEOTIDE LINKAGES
  申请人：Parang Keykavous

  公开号：US20080207551A1

  公开（公告）日：2008-08-28

  The synthesis and biochemical utility of modified oligonucleotides containing diphosphodiester internucleotide linkages. The synthesis of these compounds was carried out using diphosphitylating reagents. Oligonucleotides containing diphosphate diester bridges wherein said oligonucleotides are synthesized via a solid-phase synthesis strategy to form modified oligonucleotides. Diphosphitylating, triphosphitylating, tetraphosphitylating, β-triphosphitylating, bifunctional diphosphitylating, bifunctional triphosphitylating, and bifunctional tetraphosphitylating reagents wherein, the phosphorus atoms are linked together through oxygen, sulfur, amino, or methylene groups and/or are substituted with chlorine, diisopropylamine and cyanoethoxy groups.

  含有二磷酸二酯间核苷酸连接的修饰寡核苷酸的合成和生物化学应用。这些化合物的合成是使用二磷酸化试剂进行的。通过固相合成策略合成含有二磷酸二酯桥的寡核苷酸来形成修饰寡核苷酸。其中，二磷酸化、三磷酸化、四磷酸化、β-三磷酸化、双官能团二磷酸化、双官能团三磷酸化和双官能团四磷酸化试剂中的磷原子通过氧、硫、氨基或亚甲基基团连接在一起，并且/或被氯、二异丙基胺和氰乙氧基基团取代。
• US8193384B2
  申请人：——

  公开号：US8193384B2

  公开（公告）日：2012-06-05
• 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.