O^5'-tert-butyldimethylsilyl-N⁴,O^2',O^3'-tribenzoylcytidine | 144002-30-2

• 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: O^5'-tert-butyldimethylsilyl-N⁴,O^2',O^3'-tribenzoylcytidine
• 英文别名: 5'-O-tert-butyldimethylsilyl-2'-O,3'-O,4-N-tribenzoylcytidine；4-N-benzoyl-2'3'-di-O-benzoyl-5'-O-t-butyldimethylsilyl cytidine；[(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 144002-30-2
• 化学式: C₃₆H₃₉N₃O₈Si
• 分子量: 669.806
• InChiKey: SLRPADZQVCZKIE-SSKIFPDDSA-N

物化性质

• 熔点：
  132-133 °C
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O^5'-tert-butyldimethylsilyl-N⁴,O^2',O^3'-tribenzoylcytidine 在 吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 217.0h， 生成
  参考文献：
  名称：

  Preparation of fluorinated RNA nucleotide analogs potentially stable to enzymatic hydrolysis in RNA and DNA polymerase assays

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2014.07.019
• 作为产物：
  描述：

  胞苷 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-N⁴,O^2',O^3'-tribenzoylcytidine
  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。
• Design and Synthesis of α-Carboxy Phosphononucleosides
  作者：Sebastien Debarge、Jan Balzarini、Anita R. Maguire

  DOI：10.1021/jo101738e

  日期：2011.1.7

  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.
• 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.