5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydro-2'-deoxyuridine | 170236-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydro-2'-deoxyuridine
• 英文别名: 2,3'-anhydro-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine
• CAS: 170236-36-9
• 化学式: C₃₀H₂₈N₂O₆
• 分子量: 512.562
• InChiKey: OHKLKAMJXPHLKV-STROYTFGSA-N

物化性质

• 沸点：
  648.4±65.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.04
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydro-2'-deoxyuridine 在 三乙烯二胺 、 4-二甲氨基吡啶 、 叠氮化锂 、 氨 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.5h， 生成 4-Amino-1-{(2R,4S,5S)-4-azido-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one
  参考文献：
  名称：

  用于制备3'-氨基修饰的寡核苷酸的新型氨基甲酸酯载体。

  摘要：

  描述了一种制备在3'-末端带有氨基的寡核苷酸的新颖方法。使用两种不同的策略制备了具有氨基烷基和通过碱不稳定的氨基甲酸酯键如2-（2-硝基苯基）乙氧基羰基和芴基甲氧基羰基连接的3'-氨基-2'，3'-二脱氧核苷的几种CPG载体。这些支持物与标准的固相亚磷酸三酯方法兼容，并产生在3'端含有氨基的寡核苷酸。讨论了3'-氨基寡核苷酸的几种特性，例如核酸酶抗性，杂交和寡核苷酸缀合物的制备。

  DOI：

  10.1016/0968-0896(96)00156-3
• 作为产物：
  描述：

  Methanesulfonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 potassium phtalimide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以80%的产率得到5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydro-2'-deoxyuridine
  参考文献：
  名称：

  用于制备3'-氨基修饰的寡核苷酸的新型氨基甲酸酯载体。

  摘要：

  描述了一种制备在3'-末端带有氨基的寡核苷酸的新颖方法。使用两种不同的策略制备了具有氨基烷基和通过碱不稳定的氨基甲酸酯键如2-（2-硝基苯基）乙氧基羰基和芴基甲氧基羰基连接的3'-氨基-2'，3'-二脱氧核苷的几种CPG载体。这些支持物与标准的固相亚磷酸三酯方法兼容，并产生在3'端含有氨基的寡核苷酸。讨论了3'-氨基寡核苷酸的几种特性，例如核酸酶抗性，杂交和寡核苷酸缀合物的制备。

  DOI：

  10.1016/0968-0896(96)00156-3

文献信息

• Thermal stabilisation of RNA·RNA duplexes and G-quadruplexes by phosphorothiolate linkages
  作者：Michael M. Piperakis、James W. Gaynor、Julie Fisher、Richard Cosstick

  DOI：10.1039/c2ob26940f

  日期：——

  The effect of 3′-S-phosphorothiolate linkages on the stability of RNA·RNA duplexes and G-quadruplex structures has been studied. 3′-Thio-2′-deoxyuridine was incorporated into RNA duplexes and thermal melting studies revealed that the resulting 3′-S-phosphorothiolate linkages increased the stability of the duplex to thermal denaturation. Additionally, and contrary to expectation, a similar effect on duplex stability was observed when the same thionucleoside was incorporated into the RNA strand of a RNA·DNA duplex. A suitably protected derivative of 3′-thio-2′-deoxyguanosine was prepared using an oxidation–reduction strategy and this residue also increased the thermal stability the [d(TGGGGT)]4 G-quadruplex when positioned centrally. The results are discussed in terms of the influence that the sulfur atom has on the conformation of the furanose ring and imply that the previously noted high thermal stability of parallel RNA quadruplexes is not derived from H-bonding interactions of the 2′-hydroxyl group, but can be attributed to conformational effects.

  关于3′-S-磷硫键对RNA·RNA双链体和G-四链体结构稳定性的影响已有研究。在RNA双链体中加入了3′-巯基-2′-脱氧尿苷，热熔解研究表明，形成的3′-S-磷硫键增强了双链体对热变性的稳定性。此外，与预期相反，当同样的硫代核苷酸被引入RNA·DNA双链体的RNA链时，也观察到类似的增强双链体稳定性的效应。通过氧化还原策略制备了适当保护的3′-巯基-2′-脱氧鸟苷衍生物，并且发现该残基位于中间位置时也能提高[d(TGGGGT)]4 G-四链体的热稳定性。研究结果就硫原子对呋喃糖环构象的影响进行了讨论，并暗示，先前注意到的高温下平行RNA四链体的稳定性并非源自2′-羟基的氢键相互作用，而可能是源自构象效应。
• PROCESS FOR PREPARING DISULPHIDES AND THIOSULPHINATES AND COMPOUNDS PREPARED
  申请人：Decout Jean-Luc

  公开号：US20090264637A1

  公开（公告）日：2009-10-22

  Process for preparing a compound of the formula (I) R1-S(O) x —S(O) y R2 in which R1 represents a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen; R2, independently of R1, represents a carbon-containing group or a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen, and x and y are selected from 0 and 1 in such a way that the sum of x and y is not more than 1, characterized in that a compound of formula (II) R1-S(O) x —R3-Si(R4)(R5)(R6) in which R3 represents a hydrocarbon chain of two carbon atoms, which is optionally unsaturated and/or substituted, and R4, R5 and R6, which are identical or different, each represent, independently of one another, a hydrocarbon group, is reacted with a compound of formula (VII) R2-S(O) y —X in which X represents a halogen, intermediate compounds, and compounds prepared.

  制备化合物的过程（I）R1-S(O)x—S(O)yR2的公式，其中R1代表一个可以被一个或多个原子和/或一个或多个含有一个或多个原子的基团取代和/或中断的分子烃基团，所述原子选自N、O、P、S、Si和X，其中X代表一个卤素；独立于R1，R2代表一个含碳基团或一个可以被一个或多个原子和/或一个或多个含有一个或多个原子的基团取代和/或中断的分子烃基团，所述原子选自N、O、P、S、Si和X，其中X代表一个卤素，x和y选自0和1，使得x和y的和不超过1，其特征在于将公式（II）R1-S(O)x—R3-Si(R4)(R5)(R6)中R3代表一个含有两个碳原子的烃链，可以是不饱和和/或取代的，R4、R5和R6，它们相同或不同，每个独立地代表一个烃基团，与公式（VII）R2-S(O)y—X中的X代表一个卤素的化合物反应，中间化合物和制备的化合物。
• Anti-retroviral and cytostatic activity of 2′,3′-dideoxyribonucleoside 3′-disulfides
  作者：Béatrice Gerland、Jérôme Désiré、Jan Balzarini、Jean-Luc Décout

  DOI：10.1016/j.bmc.2008.05.065

  日期：2008.7

  report the synthesis, antiviral and cytostatic effects of nucleosides bearing a 3'-disulfide function as prodrugs of potentially active 3'-mercaptonucleotides. The lack of the anti-HIV effects in mutant CEM/TK-cells for most of the thymidine disulfides suggests that a phosphorylation step involving thymidine kinase is necessary for the eventual antiviral activity of the thymidine nucleosides. The comparable

  在本文中，我们报道了具有3'-二硫键功能的核苷作为潜在活性3'-巯基核苷酸的前药的合成，抗病毒和抑制细胞生长的作用。对于大多数的胸苷二硫化物，突变的CEM / TK细胞缺乏抗HIV的作用，这表明，对于胸苷核苷的最终抗病毒活性，涉及胸苷激酶的磷酸化步骤是必需的。大多数二硫化物具有可比的抗HIV活性，并且它们在CEM细胞提取物中的快速还原表明2'，3'-二脱氧-3'-巯基胸苷5'-三磷酸代谢产物具有抑制作用。二硫化物在CEM / 0和Molt4 / C8细胞中的细胞抑制作用似乎强烈依赖于非核苷二硫化物部分的性质，并且在保留抗逆转录病毒活性方面降低了。
• Synthesis of 3′-<i>S</i>-Phosphorothiolate Oligonucleotides for their Potential Use in RNA Interference
  作者：James W. Gaynor、John Brazier、Rick Cosstick

  DOI：10.1080/15257770701490753

  日期：2007.11.26

  The potency of RNA interference (RNAi) undoubtedly can be improved through chemical modifications to the small interfering RNAs (siRNA). By incorporation of the 3'-S-phosphorothiolate modification into strands of RNA, it is hoped that specific regions of a siRNA duplex can be stabilised to enhance the target binding affinity of a selected antisense strand into the activated RNA-induced silencing complex (RISC*). Oligonucleotides composed entirely of this modification are desirable so unconventional 5 -> 3' synthesis is investigated, with initial solution-phase testing proving successful. The phosphoroamidite monomer required for solid-phase synthesis has also been produced.