5'-O-Dimethoxytritylthymidine-3'-O-[β-cyanoethyl-(S-2,4-dichlorobenzyl)]-phosphorodithioate | 129789-64-6

• 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: 5'-O-Dimethoxytritylthymidine-3'-O-[β-cyanoethyl-(S-2,4-dichlorobenzyl)]-phosphorodithioate
• 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-[(2,4-dichlorophenyl)methylsulfanyl]phosphinothioyl]oxypropanenitrile
• CAS: 129789-64-6
• 化学式: C₄₁H₄₀Cl₂N₃O₈PS₂
• 分子量: 868.796
• InChiKey: QVPASAULVDBHET-OSHXEJAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.94
• 重原子数：
  57.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  134.03
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  5'-O-Dimethoxytritylthymidine-3'-O-[β-cyanoethyl-(S-2,4-dichlorobenzyl)]-phosphorodithioate 在 吡啶 、 N-甲基咪唑 、 PyFNOP 、 苯硫酚 、 叔丁胺 、 三乙胺 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-sulfidophosphinothioyl]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’-(4,4’-二甲氧基三苯基)-3’-脱氧胸苷 2’-(2-氰乙基-N,N-二异丙基)亚磷酰胺 在 四氮唑 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 lutidine 、 硫化氢 、 sodium iodide 作用下， 以 甲苯 为溶剂， 生成 5'-O-Dimethoxytritylthymidine-3'-O-[β-cyanoethyl-(S-2,4-dichlorobenzyl)]-phosphorodithioate
  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

• Synthesis of dinucleoside and dinucleotide phosphorodithioates via a phosphotriester approach
  作者：Eric K. Yau、Yun-Xi Ma、M.H. Caruthers

  DOI：10.1016/s0040-4039(00)88887-5

  日期：1990.1

  -O-acetylthymidine or thymidine-3′ -O-[β-cyanoethyl-(S-2,4-dichlorobenzyl)]-phosphorodithioate, 1-methylimidazole, and 2,4,6-triisopropylbenzenesulfonylchloride react to give excellent yields of dinucleoside phosphorodithioates.

  5'-O-二甲氧基三苯甲基和S-保护的胸苷-3'-硫代磷酸二硫酯，3'-O-乙酰基胸苷或胸苷-3'-O- [β-氰基乙基-（S-2,4-二氯苄基）]-二硫代磷酸酯，1 -甲基咪唑与2,4,6-三异丙基苯磺酰氯反应生成二核苷二硫代磷酸酯的产率很高。
• 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.