2',3',5'-tri-O-acetyl-9-(β-D-ribofuranosyl)-2-fluoro-purine | 35855-11-9

• 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-9-(β-D-ribofuranosyl)-2-fluoro-purine
• 英文别名: 2-fluoro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine；2',3',5'-tri-O-acetyl-9-(β-D-ribofuranosyl)-2-fluoropurine；tri-O-acetyl-2-(2-fluoro-purin-9-yl)-β-D-1-deoxy-ribofuranose；9-(2,3,5-Tri-O-acetyl-ss-D-ribofuranosyl)-2-fluoropurin；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-fluoropurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 35855-11-9
• 化学式: C₁₆H₁₇FN₄O₇
• 分子量: 396.332
• InChiKey: MIJSDBGKUOTVRA-RGCMKSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-9-(β-D-ribofuranosyl)-2-fluoro-purine 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-9-(β-D-ribofuranosyl)-2-[2-(triphenylmethylthio)ethyl]aminopurine
  参考文献：
  名称：

  Covalent stabilization of a small molecule–RNA complex

  摘要：

  We demonstrate covalent bond formation between an RNA aptamer containing a cysteamine-tethered nucleobase and helix-threading peptides (HTPs) containing alpha-bromoacetamide N-termini. The reaction is high yielding and inhibited by a DNA strand Watson-Crick complementary to the aptamer sequence indicating covalent reaction is dependent on the high affinity HTP-binding site present in the folded aptamer. These results are important for future structural studies of HTP-RNA complexes and methods for the discovery of new high affinity analogs via covalent tethering strategies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.136
• 作为产物：
  描述：

  9-(2,3,5-Tri-0-acetyl-ss-D-ribofuranosil)-N-amino-2-fluoroadenine 在 水 、 氧气 、 copper(II) sulfate 作用下， 反应 6.0h， 以76%的产率得到2',3',5'-tri-O-acetyl-9-(β-D-ribofuranosyl)-2-fluoro-purine
  参考文献：
  名称：

  Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO₄in water

  摘要：

  首次在催化量的CuSO4存在下实现了一步简单的脱氢反应。以CuSO4 (2 mol%)为催化剂，水为溶剂，脱氢产物获得了良好的产率（66-95%）。此外，成功合成了药物 nebularine 和 Vidarabine，并且 Vidarabine 可在0.923公斤规模生产，显示出良好的工业应用潜力。

  DOI：

  10.1039/c3gc41658e

文献信息

• Synthesis of cycloalkyl substituted purine nucleosides via a metal-free radical route
  作者：Dong-Chao Wang、Ran Xia、Ming-Sheng Xie、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1039/c6ob00596a

  日期：——

  An efficient route to synthesize cycloalkyl substituted purine nucleosides was developed. This metal-free C-H activation was accomplished by tBuOOtBu initiated radical reaction. By adjusting the amount of tBuOOtBu and reaction...

  开发了合成环烷基取代的嘌呤核苷的有效途径。这种无金属的CH活化是通过tBuOOtBu引发的自由基反应完成的。通过调整tBuOOtBu的量和反应...
• Radical Route for the Alkylation of Purine Nucleosides at C6 via Minisci Reaction
  作者：Ran Xia、Ming-Sheng Xie、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/ol4033336

  日期：2014.1.17

  A highly regioselective Minisci reaction with the decarboxylative alkylation of purine nucleosides under mild conditions was developed. With 5 mol % AgNO3 as a catalyst and (NH4)2S2O8 as an oxidant, a series of purine nucleosides including ribosyl, deoxyribosyl, arabinosyl purine nucleosides worked well with primary, secondary, and tertiary aliphatic carboxylic acids.

  开发了在温和条件下具有嘌呤核苷脱羧烷基化的高度区域选择性Minisci反应。以5 mol％的AgNO 3为催化剂，以（NH 4）2 S 2 O 8为氧化剂，一系列嘌呤核苷，包括核糖基，脱氧核糖基，阿拉伯糖基嘌呤核苷，与伯，仲和叔脂肪族羧酸配合得很好。
• <i>N</i>²-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA
  作者：Hayden Peacock、Olena Maydanovych、Peter A. Beal

  DOI：10.1021/ol100019r

  日期：2010.3.5

  Nucleoside analogs that project substituents into the minor groove when incorporated into duplex RNA perturb the binding of proteins and can affect base pairing specificity. The synthesis of 2-aminopurine ribonucleoside analogs and their phosphoramidites, their incorporation into duplex RNA, their postsynthetic modification via Cu-catalyzed azide−alkyne cycloaddition (CuAAC), and their effect on duplex

  当掺入双链 RNA 时，将取代基投射到小沟中的核苷类似物会扰乱蛋白质的结合，并会影响碱基配对的特异性。描述了 2-氨基嘌呤核糖核苷类似物及其亚磷酰胺的合成、它们与双链 RNA 的结合、通过铜催化的叠氮化物-炔环加成 (CuAAC) 进行的合成后修饰，以及它们对双链稳定性和碱基配对特异性的影响。