3',5'-O,O-bis(dimethoxytrityl)-dithymidilyl-3',5'-phosphorofluoridate | 191977-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3',5'-O,O-bis(dimethoxytrityl)-dithymidilyl-3',5'-phosphorofluoridate
• 英文别名: 1-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-fluorophosphoryl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 191977-94-3
• 化学式: C₆₂H₆₂FN₄O₁₅P
• 分子量: 1153.16
• InChiKey: ABCVXFBALHLXGZ-BQFHDSMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  83
• 可旋转键数：
  22
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  208
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3',5'-O,O-bis(dimethoxytrityl)-dithymidilyl-3',5'-phosphorofluoridate 在 2-甲基苯磺酸 、 三羟甲基氨基甲烷盐酸盐 作用下， 以 氯仿 、 水 为溶剂， 反应 0.08h， 生成 胸苷酰(3'->5')胸苷铵盐
  参考文献：
  名称：

  Synthesis, chemical and enzymatic reactivity, and toxicity of dithymidylyl-3′,5′-phosphorofluoridate and -phosphorothiofluoridate

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00025-6
• 作为产物：
  描述：

  保护胸苷 在 四氮唑 、 silver fluoride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.25h， 生成 3',5'-O,O-bis(dimethoxytrityl)-dithymidilyl-3',5'-phosphorofluoridate
  参考文献：
  名称：

  Synthesis, chemical and enzymatic reactivity, and toxicity of dithymidylyl-3′,5′-phosphorofluoridate and -phosphorothiofluoridate

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00025-6

文献信息

• 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。