9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-2,6-bis-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purine | 1420352-79-9

• 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: 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-2,6-bis-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2,6-bis(4-phenyltriazol-1-yl)purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 1420352-79-9
• 化学式: C₃₂H₂₈N₁₀O₇
• 分子量: 664.637
• InChiKey: UTOOPAKQLKCWGO-QWOIFIOOSA-N

物化性质

• 沸点：
  915.9±75.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  193
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-2,6-bis-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purine 在 potassium carbonate 、 甲胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.25h， 生成 N⁶-methyl-2-(4-phenyl-1,2,3-triazol-1-yl)-9-(β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Application of 2,6-diazidopurine derivatives in the synthesis of thiopurine nucleosides

  摘要：

  2,6-Diazidopurine derivatives undergo double azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reactions to give 2,6-bis-(triazolyl)purine analogs, which undergo selective nucleophilic aromatic substitution with various thiols at C(6). This synthetic sequence produces nucleoside analogs with 6-alkyl/arylthio-2-(4-allcyl/aryl-1H-1,2,3-triazol-1-yl)purine bases. In contrast, glycosylated 2,6-diazidopurines exhibit reasonable C(2) selectivity in nucleophilic aromatic substitution with thiols. This permits the synthesis of 2-alkylthio-6-azido-purine derivatives, which after CuAAC provide the corresponding 2-alkylthio-6-triazolyl-purine analogs. The latter are also susceptible to nucleophilic aromatic substitution with amines at C(6). The above mentioned compounds are useful molecular platforms in terms of medicinal chemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.095
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 0.08h， 生成 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-2,6-bis-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purine
  参考文献：
  名称：

  1,2,3-三唑在嘌呤化学中作为离去基团：N 6-取代的-2-三唑基-腺嘌呤核苷的三步合成及其光物理性质

  摘要：

  描述了用于合成N 6-取代的-2-（1,2,3-三唑-1-基）-腺嘌呤核苷的新颖的三步法。获得了2,6-双-（1,2,3-三唑-1-基）嘌呤核苷，这些核苷在C（6）处被胺进行了区域选择性亲核芳香取代。因此，在嘌呤化学中显示1,2,3-三唑是良好的离去基团。标题化合物显示出令人感兴趣的荧光水平，量子产率高达53％。

  DOI：

  10.1016/j.tetlet.2012.11.095

文献信息

• 1,2,3-Triazoles as leaving groups: S_NAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles
  作者：Dace Cīrule、Irina Novosjolova、Ērika Bizdēna、Māris Turks

  DOI：10.3762/bjoc.17.37

  日期：——

  series of substituted products was obtained in SNAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C–O and C–C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.

  设计了一种合成C6取代的2-三唑基嘌呤衍生物的新方法。 2,6-双三唑基嘌呤衍生物与O-和C-亲核试剂在温和条件下进行SN Ar反应，得​​到一系列取代产物。产物的分离收率高达87%。所开发的 C-O 和 C-C 键形成反应清楚地表明了嘌呤 C6 位上的 1,2,3-三唑基环作为离去基团的能力。
• Synthesis of purine nucleoside—amino acid conjugates and their photophysical properties
  作者：Dace Cīrule、Kristers Ozols、Oskars Platnieks、Ērika Bizdēna、Ilze Māliņa、Māris Turks

  DOI：10.1016/j.tet.2016.05.043

  日期：2016.7

  2,6-Bis-(1,2,3-triazol-1H-1-yl)purine nucleosides react at C(6) with the N- and S-termini of various amino acids by expelling the corresponding 1,2,3-triazole as a leaving group in nucleophilic aromatic substitution reaction. This gives rise to a novel type of conjugate between purine nucleosides and amino acids. The obtained amino acid—derived 6-amino-2-(1,2,3-triazol-1H-1-yl)-purine derivatives showed

  2,6-双-（1,2,3-三唑-1 H -1-基）嘌呤核苷在C（6）与各种氨基酸的N-和S-末端反应，通过排出相应的1,2， 3-三唑作为亲核芳族取代反应中的离去基团。这产生了嘌呤核苷和氨基酸之间的新型缀合物。获得的氨基酸衍生的6-氨基-2-（1,2,3-三唑-1 H -1-基）-嘌呤衍生物显示有用的荧光水平，量子产率高达38％，斯托克斯位移高达91 nm 。谷胱甘肽和一个含半胱氨酸的九肽选择性地与它们的S-末端反应，并产生预期的C（6）缀合物，收率很好。
• Synthesis of Novel 2- And 6-Alkyl/Arylthiopurine Derivatives
  作者：Irina Novosjolova、Ērika Bizdēna、Māris Turks

  DOI：10.1080/10426507.2014.989435

  日期：2015.8.3

  Synthetic methodologies toward different types of novel 2- and 6-alkyl/arylthiopurine nucleosides, including those containing 1,2,3-triazolyl moieties, are described. The title compounds were obtained by SNAr reactions between 2,6-diazido-, 2,6-dichloro- and 2,6-bis-triazolylpurine nucleosides and different S-nucleophiles. The chemical reactivity of the aforementioned variously substituted purine nucleosides toward different S-nucleophiles is discussed. The obtained monoazido purine nucleoside intermediates exist in azide and tetrazole tautomeric forms. These compounds were later used in 1,3-dipolar cycloaddition reactions with different terminal alkynes. The obtained sulfur-containing nucleoside analogs are interesting in terms of medicinal chemistry.