di-N-3,O-3'-benzoyl-5'-O-tert-butyldimethylsilylthymidine | 741687-35-4

• 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: di-N-3,O-3'-benzoyl-5'-O-tert-butyldimethylsilylthymidine
• 英文别名: 5′-O-tert-butyldimethylsilyl-3′-O,3-dibenzoylthymidine；[(2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 741687-35-4
• 化学式: C₃₀H₃₆N₂O₇Si
• 分子量: 564.711
• InChiKey: VNAGXDWBLKVHHX-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  di-N-3,O-3'-benzoyl-5'-O-tert-butyldimethylsilylthymidine 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以100 %的产率得到3,3'-O,N-dibenzoylthymidine
  参考文献：
  名称：

  5'-胸苷共轭甲酰基苯基硼酸作为潜在赖氨酸靶向亚氨基硼酸盐可逆共价酶探针的合成

  摘要：

  设计可逆共价分子以选择性地靶向酶或蛋白质中赖氨酸残基的 ε-氨基功能是一个非常理想的目标。在此，我们描述了用于制备一系列 5'-胸苷连接的甲酰苯基硼酸作为探针的合成方法，以检测识别胸苷的糖核苷酸加工酶。第一种合成策略通过利用 5'-叠氮胸苷的直接制备、分离和反应性，减轻了对胸苷保护基团操作的需要。通过炔丙基或乙炔基苯基酮衍生的硼酸安装炔烃环加成伙伴。第二种策略通过使用 Mitsunobu 条件和 3'- O安装的醚键将甲酰基苯基硼酸直接连接到 5-胸苷,3-二苯甲酰胸苷。用选定的探针观察到亚氨基硼酸盐的形成。

  DOI：

  10.1021/acs.joc.2c01000
• 作为产物：
  描述：

  beta-胸苷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 di-N-3,O-3'-benzoyl-5'-O-tert-butyldimethylsilylthymidine
  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

• One step selective 5′-O-allylation of thymidine using microwave or ultrasound activation
  作者：Vincent Roy、Ludovic Colombeau、Rachida Zerrouki、Pierre Krausz

  DOI：10.1016/j.carres.2004.04.008

  日期：2004.7

  An improved procedures for the synthesis of 5'-O-allylthymidine via one step selective allylation of thymidine using either ultrasound or microwave activation is described. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.
• Synthesis of 5′-Thymidine-Conjugated Formylphenylboronic Acids as Potential Lysine Targeting Iminoboronate Reversible Covalent Enzyme Probes
  作者：Alana M. M. Rangaswamy、Michael H. R. Beh、Ebrahim Soleimani、Steve Sequeira、Julie Cormier、Katherine N. Robertson、David L. Jakeman

  DOI：10.1021/acs.joc.2c01000

  日期：2022.11.4

  reversible-covalent molecules to selectively target the ε-amino functionality of lysine residues in enzymes or proteins is a highly desirable goal. Herein, we describe synthetic methodology used to prepare a series of 5′-thymidine-linked formylphenylboronic acids as probes to interrogate sugar nucleotide processing enzymes that recognize thymidine. The first synthetic strategy mitigated the need for protecting

  设计可逆共价分子以选择性地靶向酶或蛋白质中赖氨酸残基的 ε-氨基功能是一个非常理想的目标。在此，我们描述了用于制备一系列 5'-胸苷连接的甲酰苯基硼酸作为探针的合成方法，以检测识别胸苷的糖核苷酸加工酶。第一种合成策略通过利用 5'-叠氮胸苷的直接制备、分离和反应性，减轻了对胸苷保护基团操作的需要。通过炔丙基或乙炔基苯基酮衍生的硼酸安装炔烃环加成伙伴。第二种策略通过使用 Mitsunobu 条件和 3'- O安装的醚键将甲酰基苯基硼酸直接连接到 5-胸苷,3-二苯甲酰胸苷。用选定的探针观察到亚氨基硼酸盐的形成。