Dithiophosphoric acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O'-(2-cyano-ethyl) ester S-(1-methyl-1H-imidazol-2-ylmethyl) ester | 189144-44-3

• 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: Dithiophosphoric acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O'-(2-cyano-ethyl) ester S-(1-methyl-1H-imidazol-2-ylmethyl) ester
• 英文别名: 3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[(1-methylimidazol-2-yl)methylsulfanyl]phosphinothioyl]oxypropanenitrile
• CAS: 189144-44-3
• 化学式: C₃₉H₄₂N₅O₈PS₂
• 分子量: 803.897
• InChiKey: XNFMGQYRTWAGPX-CQKWZSLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  55.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  151.85
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Dithiophosphoric acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O'-(2-cyano-ethyl) ester S-(1-methyl-1H-imidazol-2-ylmethyl) ester 在 N-甲基咪唑 、 PyFNOP 、 叔丁胺 作用下， 以 吡啶 、 乙腈 为溶剂， 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-[(1-methylimidazol-2-yl)methylsulfanyl]phosphinothioyl]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：

  在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 lutidine 、 sodium iodide 作用下， 以 甲苯 为溶剂， 生成 Dithiophosphoric acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O'-(2-cyano-ethyl) ester S-(1-methyl-1H-imidazol-2-ylmethyl) ester
  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

文献信息

• Solution Phase Synthesis of Dithymidine Phosphorodithioate Using New S-Protecting Groups in Combination with a Chemoselective Coupling Reagent (PyNOP)
  作者：Jan Kehler、Ask Püschl、Otto Dahl

  DOI：10.1080/07328319708002518

  日期：1997.1

  A method for the synthesis of O-thymidin-3'-yl S-alkyl dithiophosphate monomers 1 with different S-protecting groups has been developed. These for solution phase synthesis of dithymidine phosphorodithioate by a new method. Coupling reactions are fast (15 min.) and the products phosphorothioate contaminations.