(tetra-n-butylammonium) hydrogen uridine monophosphate | 1206691-01-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: (tetra-n-butylammonium) hydrogen uridine monophosphate
• 英文别名: [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate;tetrabutylazanium
• CAS: 1206691-01-1
• 化学式: C₉H₁₂N₂O₉P*C₁₆H₃₆N
• 分子量: 565.645
• InChiKey: HCFSXUYFBPLAEZ-DYIFJOFMSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (tetra-n-butylammonium) hydrogen uridine monophosphate 在 N-甲基咪唑 、 2,4,6-三甲基苯磺酰氯 、 trimetaphosphate tri-tetrabutylammonium salt 、 水 、 乙酸–三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 guanosine-5’-tetraphosphate tetraammonium salt
  参考文献：
  名称：

  Synthesis of Nucleoside Tetraphosphates and Dinucleoside Pentaphosphates via Activation of Cyclic Trimetaphosphate

  摘要：

  A procedure for the synthesis of dinucleoside 5'-pentaphosphates (Np5N) and nucleoside 5'-tetraphosphates (Np-4) is described. The procedure relies on the activation of cyclic trimetaphosphate followed by a reaction with a nucleoside 5'-monophosphate (NMP) to give intermediates of type 3. Reaction of 3 with water or an NMP gives the desired products in yields ranging from 77 to 86%.

  DOI：

  10.1021/ol4007822

文献信息

• Iterative Synthesis of Nucleoside Oligophosphates with Phosphoramidites
  作者：Gregor S. Cremosnik、Alexandre Hofer、Henning J. Jessen

  DOI：10.1002/anie.201306265

  日期：2014.1.3

  P‐Amidites can be used in iterative couplings to selectively give mixed PIII–PV anhydrides. These intermediates can be oxidized followed by a rapid removal of the two terminal fluorenylmethyl groups. An iterative synthesis (coupling, oxidation, deprotection) of nucleoside oligophosphates can be carried out in solution and on a solid support. The coupling rates and yields are high, the procedures convenient

  P-酰胺可用于迭代偶联，以选择性地产生混合的P III -P V酸酐。这些中间体可以被氧化，然后快速除去两个末端芴基甲基。核苷低聚磷酸的迭代合成（偶联，氧化，脱保护）可以在溶液中和在固体载体上进行。偶联率和收率高，操作简便（非干燥试剂和溶剂，环境条件，未保护的核苷酸），并且纯化非常简单。该方法适用于所有规范的核苷，并有望大大简化通常烦人的P-酸酐键构建过程。
• Chemoselective Dimerization of Phosphates
  作者：Alexandre Hofer、Elia Marques、Nicole Kieliger、Sarah-Kirsten N. Gatter、Sara Jordi、Elena Ferrari、Manuel Hofmann、Teresa B. Fitzpatrick、Michael O. Hottiger、Henning J. Jessen

  DOI：10.1021/acs.orglett.6b01466

  日期：2016.7.1

  A methodology for the synthesis of oligophosphate conjugates using phosphordiamidites is described. This strategy facilitates the straightforward preparation of C2-symmetric dinucleoside tri-, penta-, and heptaphosphates. Moreover, unsymmetric compounds such as thiamine adenosine triphosphate and thiamine cytidine triphosphate can be prepared. The material is used to study the inhibitory activity of

  描述了使用亚磷酰胺合成磷酸低聚缀合物的方法。该策略促进了C 2对称二核苷三磷酸，五磷酸和七磷酸的直接制备。此外，可以制备不对称化合物，例如硫胺素三磷酸腺苷和硫胺素胞苷三磷酸。该材料用于研究硫氨化核苷酸对二磷酸腺苷核糖基转移酶的抑制活性。
• Synthesis of Nucleoside Di- and Triphosphates and Dinucleoside Polyphosphates with <i>cyclo</i>Sal-Nucleotides
  作者：Svenja Warnecke、Chris Meier

  DOI：10.1021/jo802348h

  日期：2009.4.17

  A new and efficient method for the synthesis of nucleoside di- and triphosphates as well as dinucleoside polyphosphates (NpnN′) is described. 5-Acceptor-substituted (5-nitro and 5-chloro) cycloSal-nucleotides are used as starting material that were reacted with a variety of phosphate nucleophiles as pyrophosphate or nucleotides to the corresponding products in short times and very good yields. After

  描述了一种合成核苷二磷酸和三磷酸以及二核苷多磷酸（Np n N'）的新的有效方法。5-受体取代的（5-硝基和5-氯）环Sal核苷酸被用作起始原料，可与各种磷酸盐亲核试剂（如焦磷酸盐或核苷酸）在短时间内以非常高的收率反应成相应的产物。在消耗了起始的环式Sal-磷酸三酯之后，首先将保护基团裂解，最后通过RP柱色谱分离产物。给出了在天然核苷中发现的所有五个嘧啶和嘌呤碱基以及一个非天然嘧啶碱基的实例，以证明该方法可以普遍应用。
• Synthesis of Nucleoside Tetraphosphates and Dinucleoside Pentaphosphates via Activation of Cyclic Trimetaphosphate
  作者：Samy Mohamady、Scott D. Taylor

  DOI：10.1021/ol4007822

  日期：2013.6.7

  A procedure for the synthesis of dinucleoside 5'-pentaphosphates (Np5N) and nucleoside 5'-tetraphosphates (Np-4) is described. The procedure relies on the activation of cyclic trimetaphosphate followed by a reaction with a nucleoside 5'-monophosphate (NMP) to give intermediates of type 3. Reaction of 3 with water or an NMP gives the desired products in yields ranging from 77 to 86%.