O^5'-tert-butyldimethylsilyl-N⁶,N⁶,O^3'-tribenzoyl-2'-deoxyadenosine | 1031809-78-5

• 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: O^5'-tert-butyldimethylsilyl-N⁶,N⁶,O^3'-tribenzoyl-2'-deoxyadenosine
• 英文别名: adenosine N,N-dibenzoyl-2'-deoxy-5'-O-tert-butyldimethylsilyl-3'-benzoate；5'-O-tert-butyldimethylsilyl-3'-O,6-N,N-tribenzoyl-2'-deoxyadenosine；O5'-tert-butyldimethylsilyl-N6,N6,O3'-tribenzoyl-2'-deoxyadenosine；[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-[6-(dibenzoylamino)purin-9-yl]oxolan-3-yl] benzoate
• CAS: 1031809-78-5
• 化学式: C₃₇H₃₉N₅O₆Si
• 分子量: 677.832
• InChiKey: PUFLNAVRRFKTLX-FRXPANAUSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  770.5±70.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  126
• 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-N⁶,N⁶,O^3'-tribenzoyl-2'-deoxyadenosine 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N⁶,N⁶,O^3'-tribenzoyl-2'-deoxyadenosine
  参考文献：
  名称：

  多苯甲酰化核苷的新型合成方法

  摘要：

  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。

  DOI：

  10.1080/00397910801916280
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 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-N⁶,N⁶,O^3'-tribenzoyl-2'-deoxyadenosine
  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。
• Decoding the Logic of the tRNA Regiospecificity of Nonribosomal FemXWv Aminoacyl Transferase
  作者：Matthieu Fonvielle、Maryline Chemama、Maxime Lecerf、Régis Villet、Patricia Busca、Ahmed Bouhss、Mélanie Ethève-Quelquejeu、Michel Arthur

  DOI：10.1002/anie.201001473

  日期：——

  Natural selection: Replacement of the 3′‐OH group of Ala‐tRNAAla with 3′‐H affected FemXWv‐catalyzed aminoacyl transfer from the 2′‐position, but not substrate binding. The ability of FemXWv to bind and transacylate the 3′‐O‐Ala isomer initially formed by alanyl‐tRNA synthetase (AlaRS) may be crucial for efficient competition with the ribosome (see scheme).

  自然选择：用3'-H影响的FemX Wv催化的氨基酰基从2'-位转移来取代Ala-tRNA Ala的3'-OH基团，但不影响底物结合。FemX Wv结合并通过丙氨酰tRNA合成酶（AlaRS）最初形成的3'-O-Ala异构体的能力可能对与核糖体的有效竞争至关重要（请参阅方案）。
• 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.