| 1399820-28-0

• 分子结构分类: 有机化合物 - 苯类化合物
• CAS: 1399820-28-0
• 化学式: C₂₆H₂₇N₂O₈P
• 分子量: 526.483
• InChiKey: UUJQTDXMYJLHSK-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  125.92
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 三乙胺 作用下， 以 乙腈 为溶剂， 以98.8%的产率得到3'-O-acetylthymidine-5'-O-H-phosphonate
  参考文献：
  名称：

  Oxidation of H-Phosphonates with Iodine by Intramolecular Support of a 2-Pyridyl Thermolabile Protecting Group

  摘要：

  Acceleration of H-phosphonate diester oxidation with iodine accompanied by a thermolabile protecting group (TPG) is presented. It is shown that the intermediate product of this reaction is an oxazaphospholidine oxide which forms a phosphate diester only when a 2-pyridyl TPG is applied. The intermediate product is formed with exocyclic nitrogen. The absolute configurations of phosphorothioate diesters, H-phosphonate diesters, and oxazaphospholidine oxides were determined. P-31 NMR spectroscopy was used to evaluate the relationship between chemical shift and absolute configuration at the phosphorus center of H-phosphonate diesters and oxazaphospholidine oxides.

  DOI：

  10.1021/jo300937k
• 作为产物：
  描述：

  ammonium (9H-fluoren-9-yl)methyl H-phosphonate 、 3'-O-acetylthymidine 在 吡啶 、 三乙胺 、 三甲基乙酰氯 作用下， 以 二氯甲烷 为溶剂， 以65.5%的产率得到
  参考文献：
  名称：

  Oxidation of H-Phosphonates with Iodine by Intramolecular Support of a 2-Pyridyl Thermolabile Protecting Group

  摘要：

  Acceleration of H-phosphonate diester oxidation with iodine accompanied by a thermolabile protecting group (TPG) is presented. It is shown that the intermediate product of this reaction is an oxazaphospholidine oxide which forms a phosphate diester only when a 2-pyridyl TPG is applied. The intermediate product is formed with exocyclic nitrogen. The absolute configurations of phosphorothioate diesters, H-phosphonate diesters, and oxazaphospholidine oxides were determined. P-31 NMR spectroscopy was used to evaluate the relationship between chemical shift and absolute configuration at the phosphorus center of H-phosphonate diesters and oxazaphospholidine oxides.

  DOI：

  10.1021/jo300937k

文献信息

• A practical synthesis of nucleoside 5′-diphosphates from nucleoside 5′-<i>H</i>-phosphonate monoesters
  作者：Marta Rachwalak、Malgorzata Rozniewska、Justyna Golebiewska、Tomasz Jakubowski、Michal Sobkowski、Joanna Romanowska

  DOI：10.1080/00397911.2020.1814817

  日期：2020.12.16

  and convenient synthetic protocols based on H-phosphonate chemistry have been developed for the preparation of nucleoside 5′-diphosphates. It consists of oxidation of the silylated H-phosphonate monoesters in pyridine with iodine to produce the corresponding N-pyridiniumphosphonate intermediates, followed by their reactions with orthophosphoric acid used as a nucleophile. The added value of the method

  摘要 已经开发了一种基于 H-膦酸酯化学的简单方便的合成方案，用于制备核苷 5'-二磷酸。它包括在吡啶中用碘氧化甲硅烷基化的 H-膦酸酯单酯以产生相应的 N-吡啶鎓膦酸酯中间体，然后它们与用作亲核试剂的正磷酸反应。该方法的附加值是反应的底物 H-膦酸酯单酯可以由相应的核苷原位制备，无需分离即可用于下一步。该方法简单，适用于核糖和脱氧核糖核苷的各种二磷酸盐及其类似物的制备。图形概要