3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[(2,4-dichlorophenyl)methylsulfanyl]phosphoryl]oxypropanenitrile | 133729-38-1

• 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-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[(2,4-dichlorophenyl)methylsulfanyl]phosphoryl]oxypropanenitrile
• CAS: 133729-38-1
• 化学式: C₄₁H₄₀Cl₂N₃O₉PS
• 分子量: 852.729
• InChiKey: ARFKHPIBQMNYBM-GHFFOPBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  171
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[(2,4-dichlorophenyl)methylsulfanyl]phosphoryl]oxypropanenitrile 在 N-甲基咪唑 、 三异丙基氯硅烷 、 叔丁胺 作用下， 以 吡啶 为溶剂， 反应 0.13h， 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[(2,4-dichlorophenyl)methylsulfanyl]phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
  参考文献：
  名称：

  Synthesis of Oligodeoxynucleoside Phosphoro-Monothioates and Phosphorodithioates by a Phosphotriester Method

  摘要：

  A phosphotriester method for the synthesis of dithymidine phosphoromonothioates and phosphorodithioates with new S-protecting groups has been investigated. Four of the S-protecting groups possesed catalytic activity, however side reactions occurred during deprotection. The best S-protecting group was 4-chloro-2-nitrobenzyl which could be removed with a minimum of side reactions (0.3 %). The coupling reagent PyFNOP (14) gave protected dithymidine phosphoromonothioate in 96 % yield after 15 min coupling. Furthermore PyFNOP chemoselectively activates oxygen in nucleoside phosphorodithioate monomers 9 and can be used for the synthesis of oligodeoxynucleoside phosphorodithioates with mixed base sequences.

  DOI：

  10.1080/07328319708006243
• 作为产物：
  描述：

  5'-O-(p,p'-dimethoxytrityl)thymidine 3'-(2-cyanoethyl) H-phosphonate 在 2,6-二甲基吡啶 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 sodium iodide 作用下， 以 乙腈 、 苯 为溶剂， 反应 1.0h， 生成 3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[(2,4-dichlorophenyl)methylsulfanyl]phosphoryl]oxypropanenitrile
  参考文献：
  名称：

  Solution Phase Synthesis of Dithymidine Phosphorothioate by a Phosphotriester Method Using NewS-Protecting Groups

  摘要：

  A phosphotriester method for the synthesis of dithymidine phosphorothioates with eight S-protecting groups has been investigated. Three of the S-protecting groups possesed catalytic activity, however side reactions occurred under deprotection. The best S-protecting group was 4-chloro-2-nitrobenzyl which could be removed with a minimum of side reactions (0.3%). The Coupling reagent PyFNOP (11) gave protected dithymidine phosphorothioate in 96% yield after 15 min coupling.

  DOI：

  10.1080/07328319708002529