2,2,2-trichloroethyl (NE)-N-[[[(2R,3S,5R)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylamino]-[[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(E)-N-[2-(2-hydroxyethoxy)ethyl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]amino]methylidene]carbamate | 210821-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,2,2-trichloroethyl (NE)-N-[[[(2R,3S,5R)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylamino]-[[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(E)-N-[2-(2-hydroxyethoxy)ethyl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]amino]methylidene]carbamate
• CAS: 210821-55-9
• 化学式: C₁₁₆H₁₃₉Cl₂₄N₄₁O₄₂
• 分子量: 3630.5
• InChiKey: IQFMOFAXHBVZGK-JXMFAADBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  223
• 可旋转键数：
  68
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  1030
• 氢给体数：
  26
• 氢受体数：
  43

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl (NE)-N-[[[(2R,3S,5R)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylamino]-[[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(E)-N-[2-(2-hydroxyethoxy)ethyl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]amino]methylidene]carbamate 在 溶剂黄146 、 镉 作用下， 反应 1.0h， 以1.6 mg的产率得到1-[[(2R,3S,5R)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]-3-[(2R,3S,5R)-2-[[[N-[(2R,3S,5R)-2-[[[N-[(2R,3S,5R)-2-[[[N-[(2R,3S,5R)-2-[[[N-[(2R,3S,5R)-2-[[[N-[(2R,3S,5R)-2-[[[N-[(2R,3S,5R)-2-[[[N-[2-(2-hydroxyethoxy)ethyl]carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]guanidine
  参考文献：
  名称：

  脱氧核胍 (DNG) 寡聚体的固相合成和八聚胸苷寡聚体与 DNA 寡聚体结合保真度的熔点和圆二色性分析

  摘要：

  报道了一种实用的固相合成脱氧核胍 (DNG)，一种带正电荷的 DNA 骨架类似物。DNG 固相合成中的核苷偶联步骤涉及末端 3'-胺对电子激活的 5'-碳二亚胺的攻击，以产生受保护的胍核苷间键。活性碳二亚胺是通过汞 (II) 从不对称取代的硫脲中提取硫而原位合成的，其中一个取代基是吸电子保护基团，另一个是 5'-核苷单体。除了碳化二亚胺之外，这还会产生硫化汞沉淀物，该沉淀物积聚在固体载体的孔中，限制溶剂和试剂的进入并降低每个连续循环的偶联产率。这一障碍通过一个简单的洗涤步骤来克服，该步骤涉及一种苯硫酚溶液，该溶液很容易去除汞盐。将这一步添加到循环中使 DNG 低聚物能够合成...

  DOI：

  10.1021/ja984212w
• 作为产物：
  描述：

  5'-(N'-trichloroethoxycarbonylthiourea)-3'-(9-fluorenylmethoxycarboxamide)-3',5'-deoxythymidine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2,2,2-trichloroethyl (NE)-N-[[[(2R,3S,5R)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylamino]-[[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(E)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(Z)-N-[(2R,3S,5R)-2-[[[(E)-N-[2-(2-hydroxyethoxy)ethyl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N'-(2,2,2-trichloroethoxycarbonyl)carbamimidoyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]amino]methylidene]carbamate
  参考文献：
  名称：

  脱氧核胍 (DNG) 寡聚体的固相合成和八聚胸苷寡聚体与 DNA 寡聚体结合保真度的熔点和圆二色性分析

  摘要：

  报道了一种实用的固相合成脱氧核胍 (DNG)，一种带正电荷的 DNA 骨架类似物。DNG 固相合成中的核苷偶联步骤涉及末端 3'-胺对电子激活的 5'-碳二亚胺的攻击，以产生受保护的胍核苷间键。活性碳二亚胺是通过汞 (II) 从不对称取代的硫脲中提取硫而原位合成的，其中一个取代基是吸电子保护基团，另一个是 5'-核苷单体。除了碳化二亚胺之外，这还会产生硫化汞沉淀物，该沉淀物积聚在固体载体的孔中，限制溶剂和试剂的进入并降低每个连续循环的偶联产率。这一障碍通过一个简单的洗涤步骤来克服，该步骤涉及一种苯硫酚溶液，该溶液很容易去除汞盐。将这一步添加到循环中使 DNG 低聚物能够合成...

  DOI：

  10.1021/ja984212w

文献信息

• Solid-phase synthesis of oligomeric deoxynucleic guanidine (DNG): A polycationic analogue of DNA
  作者：Barry A. Linkletter、Thomas C. Bruice

  DOI：10.1016/s0960-894x(98)00228-5

  日期：1998.6

  DNG is a DNA analogue wherein the negatively charged phosphate backbone linkages have been replaced by achiral positively charged guanidinium linkages and has high affinity for complimentary DNA. The synthesis of these compounds in solution phase has been severely limited due to diminishing yields and solubility limitations. For the first time, an efficient solid-phase synthesis for oligomeric is reported. (C) 1998 Elsevier Science Ltd. Ail rights reserved.
• Solid-Phase Synthesis of Deoxynucleic Guanidine (DNG) Oligomers and Melting Point and Circular Dichroism Analysis of Binding Fidelity of Octameric Thymidyl Oligomers with DNA Oligomers
  作者：Barry A. Linkletter、Istvan E. Szabo、Thomas C. Bruice

  DOI：10.1021/ja984212w

  日期：1999.4.1

  A practical solid-phase synthesis of deoxynucleic guanidine (DNG), a positively charged DNA backbone analogue, is reported. The nucleoside coupling step in the solid-phase synthesis of DNG involves the attack of a terminal 3‘-amine upon an electronically activated 5‘-carbodiimide to create a protected guanidinium internucleoside linkage. The activated carbodiimide is synthesized in situ by the mercury(II)

  报道了一种实用的固相合成脱氧核胍 (DNG)，一种带正电荷的 DNA 骨架类似物。DNG 固相合成中的核苷偶联步骤涉及末端 3'-胺对电子激活的 5'-碳二亚胺的攻击，以产生受保护的胍核苷间键。活性碳二亚胺是通过汞 (II) 从不对称取代的硫脲中提取硫而原位合成的，其中一个取代基是吸电子保护基团，另一个是 5'-核苷单体。除了碳化二亚胺之外，这还会产生硫化汞沉淀物，该沉淀物积聚在固体载体的孔中，限制溶剂和试剂的进入并降低每个连续循环的偶联产率。这一障碍通过一个简单的洗涤步骤来克服，该步骤涉及一种苯硫酚溶液，该溶液很容易去除汞盐。将这一步添加到循环中使 DNG 低聚物能够合成...