O^5'-tert-butyldimethylsilyl-N³,O^2',O^3'-tribenzoyluridine | 201664-47-3

• 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: O^5'-tert-butyldimethylsilyl-N³,O^2',O^3'-tribenzoyluridine
• 英文别名: 5'-O-tert-butyldimethylsilyl-2',3'-O,3-N-tribenzoyluridine；3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-tert-butyldimethylsilyl-uridine；[(2R,3R,4R,5R)-5-(3-benzoyl-2,4-dioxopyrimidin-1-yl)-4-benzoyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 201664-47-3
• 化学式: C₃₆H₃₈N₂O₉Si
• 分子量: 670.791
• InChiKey: PRGNCFAEQSRNIW-SSKIFPDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O^5'-tert-butyldimethylsilyl-N³,O^2',O^3'-tribenzoyluridine 在 (氯亚甲基)二甲基氯化铵 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Transprotection of N-Benzoylated Nucleobase Derivatives by Dialkylaminomethylene Group

  摘要：

  The use of(chloromethylene)dialkylammonium chloride in selective transprotection of N-benzoylated nucleobase derivatives is reported along with the evaluation of the stability of various protecting groups widely used in nucleoside and/or nucleotide chemistry.

  DOI：

  10.1080/07328319708002565
• 作为产物：
  描述：

  尿嘧啶核苷 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 O^5'-tert-butyldimethylsilyl-N³,O^2',O^3'-tribenzoyluridine
  参考文献：
  名称：

  Design and Synthesis of α-Carboxy Phosphononucleosides

  摘要：

  Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.

  DOI：

  10.1021/jo101738e

文献信息

• Novel Synthetic Approach to Multibenzoylated Nucleosides
  作者：Xue‐Feng Zhu、A. Ian Scott

  DOI：10.1080/00397910801916280

  日期：2008.4

  Abstract An improved and highly efficient synthetic approach to multibenzoylated nucleosides bearing free 5′‐hydroxyl groups is described here. By employing t-butyldimethylsilyl (TBDMS) rather than the more commonly used dimethoxytrityl (DMTr) as a temporary 5′‐OH protecting group of the starting nucleoside, this methodology provides the expected products in nearly quantitative yields, thereby substantially

  摘要 这里描述了一种改进的、高效的带有游离 5'-羟基的多苯甲酰化核苷的合成方法。通过使用叔丁基二甲基甲硅烷基 (TBDMS) 而不是更常用的二甲氧基三苯甲基 (DMTr) 作为起始核苷的临时 5'-OH 保护基团，该方法以接近定量的产率提供了预期的产品，从而大大降低了成本和工作量的合成。
• Preparation of fluorinated RNA nucleotide analogs potentially stable to enzymatic hydrolysis in RNA and DNA polymerase assays
  作者：Anton Shakhmin、John-Paul Jones、Inessa Bychinskaya、Mikhail Zibinsky、Keriann Oertell、Myron F. Goodman、G.K. Surya Prakash

  DOI：10.1016/j.jfluchem.2014.07.019

  日期：2014.11

  Analogs of ribonucleotides (RNA) stable to enzymatic hydrolysis were prepared and characterized. Computational investigations revealed that this class of compounds with a modified triphosphate exhibits the correct polarity and minimal steric effects compared to the natural molecule. Non-hydrolysable properties as well as the ability of the modified nucleotide to be recognized by enzymes were probed by performing single-turnover gap filling assays with T7 RNA polymerase and DNA polymerase beta. (C) 2014 Elsevier B.V. All rights reserved.
• Grec, Marta; Swierk, Piotr; Pastuch, Gabriela, Acta poloniae pharmaceutica, 2010, vol. 67, # 6, p. 652 - 663
  作者：Grec, Marta、Swierk, Piotr、Pastuch, Gabriela、Szeja, Wieslaw

  DOI：——

  日期：——