4-(p-nitrophenoxy)-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one | 189005-86-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-(p-nitrophenoxy)-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one
• 英文别名: 2'-deoxy-4-O-(4-nitrophenyl)uridine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(4-nitrophenoxy)pyrimidin-2-one
• CAS: 189005-86-5
• 化学式: C₁₅H₁₅N₃O₇
• 分子量: 349.3
• InChiKey: PROOHNTWAMXJHF-OUCADQQQSA-N

物化性质

• 沸点：
  597.1±60.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  136.95
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-(p-nitrophenoxy)-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 在 硫化氢 作用下， 以 甲醇 、 三乙胺 为溶剂， 反应 1.0h， 以97%的产率得到4-硫代胸苷
  参考文献：
  名称：

  Convenient Intermediates for the Preparation ofC-4 Modified Derivatives of Pyrimidine Nucleosides

  摘要：

  4-(4-Nitrophenoxy)-1-(beta-D-ribofuranosyl)pyrimidin-2(1H)-one 15, 5-methyl-4-(1,2,4-triazol-1-yl)-1-(beta-D-2-deoxyribofuranosyl 7a and 4-(4-nitrophenoxy)-1-(beta-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 17a, respectively, have been prepared and are recommended as reactive intermediates for the preparation of derivatives of uridine, thymidine and 2'-deoxyuridine which are modified at C-4.

  DOI：

  10.1080/07328319708002521
• 作为产物：
  描述：

  以 甲醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 10.5h， 生成 4-(p-nitrophenoxy)-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Convenient Intermediates for the Preparation ofC-4 Modified Derivatives of Pyrimidine Nucleosides

  摘要：

  4-(4-Nitrophenoxy)-1-(beta-D-ribofuranosyl)pyrimidin-2(1H)-one 15, 5-methyl-4-(1,2,4-triazol-1-yl)-1-(beta-D-2-deoxyribofuranosyl 7a and 4-(4-nitrophenoxy)-1-(beta-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 17a, respectively, have been prepared and are recommended as reactive intermediates for the preparation of derivatives of uridine, thymidine and 2'-deoxyuridine which are modified at C-4.

  DOI：

  10.1080/07328319708002521

文献信息

• Synthesis of new OBAN's and further studies on positioning of the catalytic group
  作者：Hans Åström、Roger Strömberg

  DOI：10.1039/b403652b

  日期：——

  extending from the C-5 position of uridine moieties, one placed internally and the other at the at the 5'-end of the oligonucleotide. The key step in the synthesis of the OBAN systems is conjugation of the catalytic group to the respective amino linkers of the modified oligonucleotides. This is achieved by first converting the 5-amino-2,9-dimethylphenanthroline to the phenylcarbamate. The reaction of this

  已经合成了两种基于锌离子的新的依赖寡核苷酸的人工核酸酶（OBAN）。这些由通过尿素接头与5-氨基-2,9-二甲基菲咯啉（新古嘌呤）缀合的2'-O-甲基修饰的RNA寡聚物组成。OBAN 4在内部胞嘧啶部分的C-4延伸的连接子上带有催化基团。OBAN 5具有两个连接的新cuproine单元，每个单元均从尿苷部分的C-5位置延伸，一个位于内部，另一个位于寡核苷酸的5'末端。OBAN系统合成中的关键步骤是将催化基团与修饰的寡核苷酸的相应氨基接头缀合。这是通过首先将5-氨基-2,9-二甲基菲咯啉转化为苯基氨基甲酸酯来实现的。该新cuproine phenylcarBAmate与在水性缓冲液（pH 8.5）中带有一个或两个伯脂族胺的寡核苷酸的反应导致尿素连接的结合物几乎定量形成。发现两个OBAN系统均在存在Zn（II）离子的情况下切割由靶序列非互补部分形成的突出区域中的RNA。讨论了这些系统与先前报告的系统之间的效率差异。
• Individual Isomers of Dinucleoside Boranophosphates as Synthons for Incorporation into Oligonucleotides: Synthesis and Configurational Assignment
  作者：Zinaida A. Sergueeva、Dmitri S. Sergueev、Anthony A. Ribeiro、Jack S. Summers、Barbara Ramsay Shaw

  DOI：10.1002/1522-2675(20000705)83:7<1377::aid-hlca1377>3.0.co;2-s

  日期：2000.7.5

  Individual isomers of the protected boranophosphates 5a and 5b, i.e, the N-6-benzyl-2'-deoxy-5'- O-(4,4'-dimethoxytrityl)adenosin-3'-yl 2'-deoxy-4-O-(4-nitrophenyl)uridin-5'-yl boranophosphates, were synthesized via stereospecific silylation and boronation of their H-phosphonate precursors. 2D-NMR Spectroscopic studies yielded an initial assignment of the isomer configuration, which was further confirmed unambiguously by a parallel chemical synthesis. Deprotection of the 'dimers' 5a and 5b yielded the individual [P(R)]- and [P(S)]-isomers 7a and 7b, respectively, i.e., the 2'-deoxyadenosin-3'-yl 2'-deoxycytidin-5'-yl boranophosphates. Their substrate properties toward phosphodiesterase I were identical to those of the previously characterized isomers of dithymidine boranophosphate. The protected 'dimers' 5a and Sb can be used as synthons to incorporate the boranophosphate linkage with a defined configuration to selected positions of an oligonucleotide chain.
• Synthesis and Properties of 2′-Deoxycytidine Triphosphate Carrying C-Myc Tag Sequence
  作者：Michael Hinz、Dirk Gottschling、Ramon Eritja、Hartmut Seliger

  DOI：10.1080/15257770008045445

  日期：2000.10

  The synthesis of 2'-deoxycytidine triphosphate carrying mercaptoethyl groups at position 4 of cytosine is described. This nucleoside triphosphate was reacted with a maleimido-peptide carrying the c-mye tag-sequence to yield a peptide-nucleoside triphosphate chimera. Primer extension studies showed that the nucleoside triphosphate modified with the peptide sequence is incorporated by DNA polymerases opposite guanine.