N²-isobutyryl-5'-O-tert-butyldimethylsilyl-2'-deoxyguanosine | 85326-10-9

• 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: N²-isobutyryl-5'-O-tert-butyldimethylsilyl-2'-deoxyguanosine
• 英文别名: 5'-O-TBDMS-N2-ibu-dG；N-[9-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 85326-10-9
• 化学式: C₂₀H₃₃N₅O₅Si
• 分子量: 451.598
• InChiKey: WZQWRHWLQPEBFF-BFHYXJOUSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  7

制备方法与用途

5′-O-TBDMS-N2-ibu-dG是一种核苷衍生物，可用来合成具有抗牛病毒性腹泻病毒活性的先导化合物[1]。

反应信息

• 作为反应物：
  描述：

  N²-isobutyryl-5'-O-tert-butyldimethylsilyl-2'-deoxyguanosine 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 N-(9-((2R,4S,5R)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide
  参考文献：
  名称：

  Synthesis of 3′-Azido-3′-Deoxythymidine-Terminated Oligonucleotide

  摘要：

  A method of completely chemical synthesis of 3'-azido-3'-deoxythymidine-terminated oligonucleotides via 5'-H-phosphonate of AZT is described.

  DOI：

  10.1080/07328319808004703
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 吡啶 、 ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 N²-isobutyryl-5'-O-tert-butyldimethylsilyl-2'-deoxyguanosine
  参考文献：
  名称：

  CN116854749

  摘要：

  公开号：

文献信息

• [EN] NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS<br/>[FR] NOUVEAUX RÉACTIFS À BASE DE PHOSPHORE (V), LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION DANS LA FABRICATION DE COMPOSÉS ORGANOPHOSHOREUX (V) STÉRÉODÉFINIS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2019200273A1

  公开（公告）日：2019-10-17

  The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.

  本发明涉及新型磷（V）（P(V)）试剂，其制备方法以及利用这种新型试剂制备有机磷（V）化合物的方法。
• Synthesis of Benzodithiol-2-yl-Substituted Nucleoside Derivatives as Lead Compounds Having Anti-Bovine Viral Diarrhea Virus Activity
  作者：Kohji Seio、Takahide Sasaki、Koichirou Yanagida、Masanori Baba、Mitsuo Sekine

  DOI：10.1021/jm049677d

  日期：2004.10.1

  Nucleoside derivatives having a benzodithiol-2-yl (BDT) group were synthesized and examined for their anti-bovine viral diarrhea virus (BVDV) activities. Other substituents structurally similar to the BDT group such as 1,3-benzodioxol-2-yl, benzimidazol-2-yl and 1-oxo-benzodithiol-2-yl groups were not effective as the pharmacophore. The anti-BVDV assay revealed that 2'-O-BDT-guanosine and 2'-O-BDT-inosine

  合成具有苯并二硫醇-2-基（BDT）基团的核苷衍生物，并检查其抗牛病毒性腹泻病毒（BVDV）的活性。结构上与BDT基团相似的其他取代基，例如1，3-苯并二恶唑-2-基，苯并咪唑-2-基和1-氧-苯并二硫醇-2-基均不能用作药效基团。抗BVDV分析表明，在本研究合成的核苷衍生物中，2'-O-BDT-鸟苷和2'-O-BDT-肌苷具有最强的抗BVDV活性。由于BVDV已被公认是人类丙型肝炎病毒（HCV）的替代物，因此BDT修饰的核苷可能成为寻找核苷型抗HCV药物（如病毒唑）的一类新型先导化合物。
• [EN] DESIGN AND SYNTHESIS OF NOVEL DISULFIDE LINKER BASED NUCLEOTIDES AS REVERSIBLE TERMINATORS FOR DNA SEQUENCING BY SYNTHESIS<br/>[FR] DÉRIVÉS NUCLÉOTIDIQUES ET LEURS MÉTHODES D'UTILISATION
  申请人：UNIV COLUMBIA

  公开号：WO2017058953A1

  公开（公告）日：2017-04-06

  Disclosed herein, inter alia, are compounds, compositions, and methods of use thereof in the sequencing a nucleic acid.

  在此披露的内容包括化合物、组合物以及它们在核酸测序中的使用方法。
• 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。
• Method for purifying 5' -protected 2' -deoxypurine nucleosides
  申请人：——

  公开号：US20030009028A1

  公开（公告）日：2003-01-09

  A method for efficiently purifying 5′ protected 2′-deoxypurine nucleosides, efficient production of which has previously been difficult. Impurities can be separated by obtaining the 5′ protected 2′-deoxypurine nucleoside as an inclusion crystal including a solvent such as that having a nitrile structure in order to purify the 5′ protected 2′-deoxypurine nucleoside at a high purity. This invention enables synthesis of highly purified protected deoxypurine nucleosides easily on a large scale, which has previously been performed by column chromatography method.

  一种用于高效纯化5′保护的2′-去氧嘌呤核苷的方法，先前其高效生产曾经困难。通过获得含有类似腈结构的溶剂的包含晶体，可将杂质分离以纯化5′保护的2′-去氧嘌呤核苷。该发明使得在大规模上轻松合成高纯度的保护去氧嘌呤核苷成为可能，而此前通常通过柱层析法进行。