dithymidylyl-3',5'-phosphorothiofluoridate | 244174-14-9

• 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: dithymidylyl-3',5'-phosphorothiofluoridate
• 英文别名: Dithymidine 3',5'-phosphorothiofluoridate；1-[(2R,4S,5R)-5-[[fluoro-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 244174-14-9
• 化学式: C₂₀H₂₆FN₄O₁₀PS
• 分子量: 564.485
• InChiKey: QWEJLLXHUXSHNN-GOBUZWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  208
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  dithymidylyl-3',5'-phosphorothiofluoridate 在 乙酸铵 作用下， 以 水 为溶剂， 反应 1.0h， 以60%的产率得到TpsT
  参考文献：
  名称：

  Misiura, Konrad; Szymanowicz, Daria; Stec, Wojciech J., Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S101 - S106

  摘要：

  DOI：
• 作为产物：
  描述：

  3'-O-acetylthymidine 在 ammonium hydroxide 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 triethylamine tris(hydrogen fluoride) 作用下， 以 水 、 乙腈 为溶剂， 反应 19.0h， 生成 dithymidylyl-3',5'-phosphorothiofluoridate
  参考文献：
  名称：

  Misiura, Konrad; Szymanowicz, Daria; Stec, Wojciech J., Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S101 - S106

  摘要：

  DOI：

文献信息

• Studies on enzymatic hydrolysis of thymidin-3′-yl thymidin-5′-yl phosphorofluoridates and the corresponding phosphorothiofluoridates
  作者：Konrad Misiura、Wojciech J. Stec、Martin Bollmark、Jacek Stawinski

  DOI：10.1039/a906659d

  日期：——

  Spleen or snake venom nuclease-assisted cleavage of P–F bonds in nucleotides bearing a phosphorofluoridate moiety occurs at negatively charged phosphates only.

  在脾脏或蛇毒核酸酶的辅助下，只在带负电荷的磷酸盐上裂解带有氟磷酸酯分子的核苷酸中的 PâF 键。
• A new method for the formation of the P–F bond
  作者：Martin Bollmark、Jacek Stawinski

  DOI：10.1039/a701728f

  日期：——

  Iodine-promoted desulfurization of phosphorothioate and phosphorodithioate diesters in the presence of triethylamine tris(hydrofluoride) (TAF) furnish a rapid and quantitative formation of the corresponding phosphorofluoridates and phosphorofluoridothioates; under the reaction conditions phosphoroselenoate and phosphoroselenothioate diesters undergo deselenization affording the phosphorofluoridate and phosphorofluoridothioate diesters, respectively.

  在三乙胺三（氢氟化物）（TAF）存在下，碘促进硫代磷酸酯和二硫代磷酸酯的脱硫反应，快速定量地生成相应的氟代磷酸酯和硫代磷酸酯；在反应条件下，硒代磷酸酯和硫代磷酸酯发生脱硒反应，分别生成氟代磷酸酯和硫代磷酸酯。
• New Methods for the Formation of the P-N and P-F Bonds, their Relevance to Nucleotide and Oligonucleotide Analogues Synthesis
  作者：Inger Kers、Martin Bollmark、Adam Kraszewski、Jacek Stawinski

  DOI：10.1080/10426509908546325

  日期：1999.1.1

  appropriate amines. Also, a new, convenient entry to nucleoside methylphosphonamidates, consisting of an oxidative coupling of nucleoside 3'-methylphosphinates with 5'-aminonucleosides, was investigated. Finally, iodine promoted desulfurization or deselenization of the appropriate phosphorothioate and phosphoroselenoate diesters in the presence of fluoride anion, was found to provide new means for the formation

  已经开发了两种方法来形成氨基磷酸酯，其中氮原子位于核苷酸间键的桥接位置。其中一种使用 H-膦酰胺酸酯作为中间体，另一种基于 H-膦酸酯单酯或其类似物与适当胺的氧化偶联。此外，研究了一种新的、方便的核苷甲基膦酰胺酸盐，由核苷 3'-甲基次膦酸盐与 5'-氨基核苷的氧化偶联组成。最后，发现碘在氟阴离子存在下促进了适当的硫代磷酸酯和硒代磷酸二酯的脱硫或脱硒，为形成 PF 键提供了新的手段。
• Synthesis, chemical and enzymatic reactivity, and toxicity of dithymidylyl-3′,5′-phosphorofluoridate and -phosphorothiofluoridate
  作者：Konrad Misiura、Daria Szymanowicz、Halina Kuśnierczyk

  DOI：10.1016/s0968-0896(01)00025-6

  日期：2001.6

  Dithymidylyl-3',5'-phosphorofluoridate and phosphorothiofluoridate were obtained by fluorinolysis of the P-Se bond in appropriate bisdimethoxytrityl selenomethyl esters. These compounds, which are hydrolytically unstable, are not inhibitors of snake venom, spleen phosphodiesterases and alkaline phosphatase. Neither compound is highly toxic. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A Mild Method for the Preparation of Nucleoside Phosphorofluoridate and Phosphorofluoridothioate Diesters
  作者：Martin Bollmark、Jacek Stawinski

  DOI：10.1080/07328319908044677

  日期：1999.6

  Synthesis of unprotected dinucleoside phosphorofluoridate and phosphorofluoridothioates from the corresponding phosphororthioate and phosphorodithioate derivatives is described.