N,N-diethylethanamine;[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] phosphono hydrogen phosphate

• 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: N,N-diethylethanamine;[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] phosphono hydrogen phosphate
• 化学式: 4C₆H₁₅N*C₁₀H₁₇N₂O₁₄P₃
• 分子量: 886.938
• InChiKey: YEDZTHKGCOEIPH-HNPMAXIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  247.38
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N,N-diethylethanamine;[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] phosphono hydrogen phosphate 在 sodium perchlorate 作用下， 以 丙酮 为溶剂， 以7.9 g的产率得到thymidine-5′-triphosphate tetrasodium salt
  参考文献：
  名称：

  An Improved Protection-Free One-Pot Chemical Synthesis of 2′-Deoxynucleoside-5′-Triphosphates

  摘要：

  A facile, straightforward, reliable, and an efficient method for the gram-scale chemical synthesis of both purine deoxynucleotides such as 2'-deoxyguanosine-5'-triphosphate (dGTP) and 2'-deoxyadenosine-5'-triphosphate (dATP) and pyrimidine deoxynucleotides such as 2'-deoxycytidine-5'-triphosphate (dCTP), thymidine-5'-triphosphate (TTP), and 2'-deoxyuridine-5'-triphosphate (dUTP) starting from the corresponding nucleoside is described. This improved "one-pot, three step" Ludwig synthetic strategy involves the monophosphorylation of nucleoside followed by reaction with tributylammonium pyrophosphate and hydrolysis of the resulting cyclic intermediate to provide the corresponding dNTP in good yields (65%-70%).

  DOI：

  10.1080/15257770.2012.670739
• 作为产物：
  描述：

  在 三正丁胺 、 三丁基焦磷酸铵 作用下， 以 磷酸三甲酯 、 乙腈 为溶剂， 反应 0.17h， 生成 N,N-diethylethanamine;[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] phosphono hydrogen phosphate
  参考文献：
  名称：

  An Improved Protection-Free One-Pot Chemical Synthesis of 2′-Deoxynucleoside-5′-Triphosphates

  摘要：

  A facile, straightforward, reliable, and an efficient method for the gram-scale chemical synthesis of both purine deoxynucleotides such as 2'-deoxyguanosine-5'-triphosphate (dGTP) and 2'-deoxyadenosine-5'-triphosphate (dATP) and pyrimidine deoxynucleotides such as 2'-deoxycytidine-5'-triphosphate (dCTP), thymidine-5'-triphosphate (TTP), and 2'-deoxyuridine-5'-triphosphate (dUTP) starting from the corresponding nucleoside is described. This improved "one-pot, three step" Ludwig synthetic strategy involves the monophosphorylation of nucleoside followed by reaction with tributylammonium pyrophosphate and hydrolysis of the resulting cyclic intermediate to provide the corresponding dNTP in good yields (65%-70%).

  DOI：

  10.1080/15257770.2012.670739

文献信息

• Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA
  作者：S. De、E. Groaz、L. Margamuljana、M. Abramov、P. Marlière、P. Herdewijn

  DOI：10.1039/c5ob00157a

  日期：——

  The incorporation and extension of synthetically unprecedented nucleoside phosphoramidate sulfonates is demonstrated using thermophilic and mesophilic microbial polymerases.

  使用嗜热和中温微生物聚合酶展示了合成前所未有的核苷酸磷酸酰胺磺酸盐的合并和扩展。