2',3',5'-tri-O-acetyl-6-(trifluoromethyl)-9-β-D-ribofuranosyl-purine | 76513-94-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3',5'-tri-O-acetyl-6-(trifluoromethyl)-9-β-D-ribofuranosyl-purine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-(trifluoromethyl)purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 76513-94-5
• 化学式: C₁₇H₁₇F₃N₄O₇
• 分子量: 446.34
• InChiKey: BXVFPSACFKBPAD-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-6-(trifluoromethyl)-9-β-D-ribofuranosyl-purine 在 吡啶 、 TEA 、 氨 、 silver nitrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 9-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl]-6-(trifluoromethyl)-purine
  参考文献：
  名称：

  Synthesis and Analysis of RNA Containing 6-Trifluoromethylpurine Ribonucleoside

  摘要：

  [GRAPHICS]We report the synthesis of a 5 ' -DMT-2 ' -TBDMS-protected phosphoramidite of 6-trifluoromethylpurine ribonucleoside (P-TFM) and its use in the site-specific incorporation of 6-trifluoromethyipurine into RNA. Properties of P-TFM-substituted RNA suggest it will be valuable in the study of RNA structure and the binding of RNA-modifying enzymes, particularly the RNA-editing adenosine deaminases.

  DOI：

  10.1021/ol016295i
• 作为产物：
  描述：

  氟磺酰基二氟乙酸甲酯 、 6-bromonebularine triacetate 在 六甲基磷酰三胺 、 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以91%的产率得到2',3',5'-tri-O-acetyl-6-(trifluoromethyl)-9-β-D-ribofuranosyl-purine
  参考文献：
  名称：

  Synthesis and Analysis of RNA Containing 6-Trifluoromethylpurine Ribonucleoside

  摘要：

  [GRAPHICS]We report the synthesis of a 5 ' -DMT-2 ' -TBDMS-protected phosphoramidite of 6-trifluoromethylpurine ribonucleoside (P-TFM) and its use in the site-specific incorporation of 6-trifluoromethyipurine into RNA. Properties of P-TFM-substituted RNA suggest it will be valuable in the study of RNA structure and the binding of RNA-modifying enzymes, particularly the RNA-editing adenosine deaminases.

  DOI：

  10.1021/ol016295i

文献信息

• Copper-Mediated Perfluoroalkylation of Heteroaryl Bromides with (phen)CuR_F
  作者：Michael G. Mormino、Patrick S. Fier、John F. Hartwig

  DOI：10.1021/ol500422t

  日期：2014.3.21

  synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated perfluoroalkyl copper reagents, (phen)CuRF, which react with aryl iodides and aryl boronates to form the corresponding benzotrifluorides. Herein the perfluoroalkylation of a series of heteroaryl bromides with (phen)CuCF3 and (phen)CuCF2CF3 is reported. The mild reaction conditions allow the process to tolerate

  在过去的几十年里，将全氟烷基连接到有机化合物上一直是一个主要的合成目标。以前，我们的小组报道了菲咯啉连接的全氟烷基铜试剂 (phen)CuR F，它与芳基碘化物和芳基硼​​酸酯反应形成相应的三氟化苯。本文报道了一系列杂芳基溴化物与 (phen)CuCF 3和 (phen)CuCF 2 CF 3的全氟烷基化。温和的反应条件允许该过程耐受许多常见的官能团。使用 (phen)CuCF 2 CF 3 进行全氟乙基化的产率比使用 (phen)CuCF 3 进行三氟甲基化的产率略高，创建了一种生成氟代烷基杂芳烃的方法，这些杂芳烃不易从三氟乙酸衍生物中获得。
• Studies on organic fluorine compounds. Part 35. Trifluoromethylation of pyrimidine- and purine-nucleosides with trifluoromethyl–copper complex
  作者：Yoshiro Kobayashi、Kenjiro Yamamoto、Toyohira Asai、Masanori Nakano、Itsumaro Kumadaki

  DOI：10.1039/p19800002755

  日期：——

  Halogenated nucleoside derivatives were trifluoromethylated using a solution of a trifluoromethyl–copper complex, which was prepared by shaking trifluoromethyl iodide and copper powder in hexamethylphosphoric triamide and filtering off the excess of copper powder. The following trifluoromethylated nucleosides were obtained in moderate to good yields: 5-trifluoromethyl-uridine, -deoxyuridine, -cytidine

  使用三氟甲基-铜络合物的溶液将卤代的核苷衍生物进行三氟甲基化，该溶液是通过将三氟甲基碘和铜粉在六甲基磷酸三酰胺中振摇并滤出过量的铜粉而制得的。以中等至良好的产率获得以下三氟甲基化的核苷：5-三氟甲基-尿苷，-脱氧尿苷，-胞苷，-脱氧胞苷和-阿拉伯糖基胞嘧啶；8-三氟甲基-腺苷，-脱氧腺苷和-肌苷；和6-三氟甲基核呋喃呋喃糖基嘌呤。该程序提供了许多三氟甲基化合物的简单合成方法。
• Metallaphotoredox Perfluoroalkylation of Organobromides
  作者：Xiangbo Zhao、David W. C. MacMillan

  DOI：10.1021/jacs.0c09977

  日期：2020.11.18

  Ruppert-Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via

  Ruppert-Prakash 型试剂（TMSCF3、TMSC2F5 和 TMSC3F7）是容易获得、空气稳定且易于处理的氟代烷基源。在此，我们描述了这些氟烷基亲核试剂与芳基和烷基溴的温和、铜催化交叉偶联，以产生各种三氟甲基、五氟乙基和七氟丙基加合物。这种光介导的转化通过甲硅烷基-自由基介导的卤素原子提取途径进行，这使得各种空间和电子需求可变的有机溴化物的全氟烷基化成为可能。通过几种药物类似物的后期功能化证明了该方法的实用性。