3',5'-O-bis-(trimethylsilyl)-5-bromo-2'-deoxyuridine | 34279-86-2

• 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: 3',5'-O-bis-(trimethylsilyl)-5-bromo-2'-deoxyuridine
• 英文别名: 5-bromo-2'-deoxy-3',5'-bis-O-(trimethylsilyl)uridine；5-bromo-1-[(2R,4S,5R)-4-trimethylsilyloxy-5-(trimethylsilyloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 34279-86-2
• 化学式: C₁₅H₂₇BrN₂O₅Si₂
• 分子量: 451.465
• InChiKey: YNGQXRFKDDIRJC-YNEHKIRRSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  3',5'-O-bis-(trimethylsilyl)-5-bromo-2'-deoxyuridine 在 盐酸 、 正丁基锂 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 生成 beta-胸苷
  参考文献：
  名称：

  Selective alkylation of pyrimidyl dianions II: synthesis, characterization, and comparative reactivity of 3′, 5′-o-bis- tetrahydropyranyl, trimethylsilyl and tert-butyldimethylsilyl derivatives of 5-bromo-2′-deoxyuridine

  摘要：

  Three compounds which can be used as precursors for thymidine synthesis via methylation at the 5 position, including 3', 5'-o-bis(tetrahydropyranyl)-5-bromo-2'-deoxyuridine 1a, 3', 5'-o-bis-(trimethylsily)-5-bromo-2'-deoxyuridine 1b, and 3', 5'-o-bis-(t-butyldimethylsilyl)-5-bromo-2'-deoxyuridine 1c, were prepared isolated and characterized by spectroscopic methods. Alkylation with methyl iodide using an organo-lithium reagent at low temperature produced 72%, 41% and 74% of thymidine 6, respectively. Tetrahydropyranyl and t-butyldimethylsilyl ethers are found to be better precursors for introduction of a methyl group at the 5 position.

  DOI：

  10.1016/s0040-4020(01)80845-0
• 作为产物：
  描述：

  溴脲苷 在 吡啶 、 正己烷 、 氯仿 、 六甲基二硅氮烷 作用下， 反应 15.0h， 生成 3',5'-O-bis-(trimethylsilyl)-5-bromo-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 5-(dihydroxyboryl)-2'-deoxyuridine and related boron-containing pyrimidines

  摘要：

  DOI：

  10.1021/jo00206a024

文献信息

• NMR and UV Studies of 4-Thio-2′-deoxyuridine and Its Derivatives
  作者：Xiaohui Zhang、Yao-Zhong Xu

  DOI：10.3390/molecules16075655

  日期：——

  5-Substituted-4-thio-2'-deoxyuridine nucleosides have been chemically synthesized and studied by NMR and UV spectroscopy. The results have been analyzed and discussed in connection with the previous data. The imino proton signal and the carbon signal of the thiocarbonyl group in the 5-substituted-4-thio-2'-deoxyuridines were found to be at much lower field, offering a potential for monitoring these

  5-Substituted-4-thio-2'-deoxyuridine nucleosides 已被化学合成并通过 NMR 和 UV 光谱进行了研究。已经结合先前的数据对结果进行了分析和讨论。发现 5-取代-4-硫代-2'-脱氧尿苷中的亚氨基质子信号和硫代羰基的碳信号处于低得多的场中，为在 DNA 水平上监测这些修饰碱基提供了潜力。所有 4-硫代核苷在 340 nm 附近都有很强的吸收，因此可用作潜在的 UVA 诱导的抗癌剂。
• 4-Thio-5-bromo-2′-deoxyuridine: chemical synthesis and therapeutic potential of UVA-induced DNA damage
  作者：Yao-Zhong Xu、Xiaohui Zhang、Hai-Chen Wu、Andrew Massey、Peter Karran

  DOI：10.1016/j.bmcl.2003.11.069

  日期：2004.2

  4-Thio-5-bromo-2'-deoxyuridine (3a) is prepared from 5-bromo-2'-deoxyuridine (BrdU) and its key properties are explored. The thionucleoside (3a) can react readily with monobromobimane and produces high fluorescence. 3a has UV maximum absorption at 340 nm and can be incorporated into cellular DNA. The cells containing 3a become sensitive to UVA light, offering therapeutic potential for UVA-induced cell killing. (C) 2003 Elsevier Ltd. All rights reserved.
• POUPEYE, E.;COUNSELL, R. E.;LEENHEER, A. DE;SLEGERS, G.;GOETHALS, P., APPL. RADIAT. AND ISOTOP. A, 40,(1989) N, C. 57-61
  作者：POUPEYE, E.、COUNSELL, R. E.、LEENHEER, A. DE、SLEGERS, G.、GOETHALS, P.

  DOI：——

  日期：——