2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-ethynyluridine | 924890-35-7

• 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: 2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-ethynyluridine
• 英文别名: 3',5'-bis-O-(tert-butyldimethylsilyl)-5-ethynyl-2'-deoxyuridine；3',5'-di-O-tert-butyldimethylsilyl-5-ethynyl-2'-deoxyuridine；3′,5′-di-O-tert-butyldimethylsilyl-5-ethynyl-2′-deoxyuridine；1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-ethynylpyrimidine-2,4-dione
• CAS: 924890-35-7
• 化学式: C₂₃H₄₀N₂O₅Si₂
• 分子量: 480.752
• InChiKey: FJKIZJNAEPAOQI-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-ethynyluridine 、 zinc 23-iodo-1,4,8,11,15,18-hexafluoro-2,3,9,10,16,17-hexakis(perfluoroisopropyl)phthalocyaninate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以87%的产率得到{23-[2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)uridin-5-ylethynyl]-1,4,8,11,15,18-hexafluoro-2,3,9,10,16,17-hexakis(perfluoroisopropyl)phthalocyaninato}zinc
  参考文献：
  名称：

  与脱氧核糖核苷共轭的全氟异丙基锌酞菁：合成、光物理特性和体外光动力活动

  摘要：

  与脱氧核糖核苷缀合的全氟异丙基取代的锌酞菁已被合成并从光谱和生物学的角度评估为光动力治疗剂。它们在有机溶液和水溶液中均表现出不聚集、高化学稳定性和良好的荧光量子产率。初步的生物学实验表明，这些结合物是癌症光动力疗法的有希望的候选者。

  DOI：

  10.1002/ejoc.201000179
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.17h， 生成 2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-ethynyluridine
  参考文献：
  名称：

  三唑基芴标记的2'-脱氧尿苷的光物理/生物物理性质的合成与研究

  摘要：

  电子共轭含芴生物分子构建块的平面结构、有吸引力的光物理性质和稀缺性吸引了最近对合成具有调制光物理特性的三唑基芴修饰的核苷的研究兴趣。在此，我们报告了几种荧光核苷的合成，其中 2'-脱氧尿苷的 C5 通过 Sonogashira 交叉偶联和铜催化的点击反应与芴类似物进行电子共轭。对合成核苷的光物理性质的研究表明，合成的核苷中的两个在各种有机溶剂中显示出有趣的双发射特性。双发射芴核苷可能会对用于监测 DNA 微环境的核酸研究产生重大影响。此外，

  DOI：

  10.1016/j.tetlet.2021.153494

文献信息

• Aggregation-induced emission by sequence-selective assembly of cyanolated distyrylbenzene in supramolecular DNA architectures
  作者：Hülya Ucar、Hans-Achim Wagenknecht

  DOI：10.1039/d2cc01161a

  日期：——

  Cyanolated distyrylbenzene conjugated to 2′-deoxyuridine is a new building block for supramolecular DNA architectures combining aggregation-induced emission and sequence-selective binding.

  靛氰化的联苯乙烯基苯并[3,4-c]嘧啶与2'-脱氧尿嘧啶共轭，是一种新的建筑单元，用于组合诱导发光和序列选择性结合的超分子DNA结构。
• Greener photocatalytic route to azide-alkyne cycloaddition reactions: Role of hole/oxygen in air
  作者：Subhendu Sekhar Bag、Sayantan Sinha、Siddharth Singh、Animes K. Golder

  DOI：10.1016/j.tet.2023.133703

  日期：2023.12

  for base-free click reaction in the green solvent with high efficiency, selectivity and fast reaction kinetics. Thus, the synthesized heterogeneous photocatalyst based on Cu(II) ion-doped TiO2 nanocomposite [CuII@TiO2] is found to be highly efficient for carrying out azide-alkyne 1,3-dipolar cycloaddition reaction (CuAAC) in an aqueous environment without needing a base. The reaction features high product

  我们结合了 Cu I和 Cu II的特性，代表了一种独特且智能的纳米光催化系统，可作为绿色溶剂中无碱点击反应的催化剂，具有高效率、选择性和快速反应动力学。因此，基于Cu(II)离子掺杂的TiO 2纳米复合材料合成的异相光催化剂[Cu II @TiO 2 ]被发现对于在水溶液中进行叠氮-炔1,3-偶极环加成反应(CuAAC)非常有效。环境，无需基础。该反应具有产物选择性高、反应条件温和、绿色溶剂、底物范围广、周转数优异、收率高、反应动力学快、官能团相容性好等特点。从机理上讲，在光照射（λ = 400 nm）时，TiO 2纳米核将电子从其价带释放到导带，进而光化学地将 Cu(II) 还原为 Cu(I)，从而实现对 CuAAC 反应的空间和时间控制。另一方面，空气中产生的空穴和/或氧气作为绿色氧化剂维持Cu(I)至Cu(II)催化循环。因此，产生的电子和空穴的协同作用持续维持催化循环，实现对点击
• Increasing the Stability of DNA:RNA Duplexes by Introducing Stacking Phenyl-Substituted Pyrazole, Furan, and Triazole Moieties in the Major Groove
  作者：Mick Hornum、Pawan Kumar、Patricia Podsiadly、Poul Nielsen

  DOI：10.1021/acs.joc.5b01577

  日期：2015.10.2

  Consecutive incorporations of our previously published thymidine analogue, 5-(1-pheny1-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine monomer W in oligonudeotides, has demonstrated significant duplex-stabilizing properties due to its efficient staking properties in the major groove of DNA:RNA duplexes. The corresponding 2'-deoxycytidine analogue is not as well-accommodated in duplexes, however, due to its clear preference for the ring-flipped coplanar conformation. In our present work, we have used oh initio calculations to design two new building blocks, 5-(5-phenylfuran-2-yl)-2'-deoxycytidine monomer Y and 5-(1-phenyl-1H-pyrazol-3-yl)-2'-deoxycytidine monomer Z, that emulate the conformation of W. These monomers were synthesized by Suzuki-Miyaura couplings, and the pyrazole moiety was obtained in a cycloaddition from N-phenylsydnone. We show that the novel analogues Y and Z engage in efficient stacking either with themselves or with W due to a better overlap of the aromatic moieties. Importantly, we demonstrate that this translates into very thermally stable DNA:RNA duplexes, thus making Y and especially Z good candidates for improving the binding affinities of oligonudeotide-based therapeutics. Since we now have both efficiently stacking T and C analogues in hand, any purine rich stretch can be effectively targeted using these simple analogues. Notably, we show that the introduction of the aromatic rings in the major groove does not significantly change the helical geometry.
• Design, Synthesis, and Spectroscopic Investigation of Zinc Dodecakis(trifluoroethoxy)phthalocyanines Conjugated with Deoxyribonucleosides
  作者：Mamidi Ramesh Reddy、Norio Shibata、Yuki Kondo、Shuichi Nakamura、Takeshi Toru

  DOI：10.1002/anie.200603590

  日期：2006.12.11