[(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 | 184773-04-4

• 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: [(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
• CAS: 184773-04-4
• 化学式: C₄₈H₅₃N₆O₁₃PS₂
• 分子量: 1017.09
• InChiKey: GPVZWRPASQBQNC-MRUDJDBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  70
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  265
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(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 在 苯硫酚 作用下， 以 吡啶 、 三乙胺 为溶剂， 以0.8%的产率得到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 S-(1-methyl-1H-imidazol-2-ylmethyl) ester; compound with triethyl-amine
  参考文献：
  名称：

  Solution Phase Synthesis of Dithymidine Phosphorodithioate Using New S-Protecting Groups in Combination with a Chemoselective Coupling Reagent (PyNOP)

  摘要：

  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.

  DOI：

  10.1080/07328319708002518
• 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 N-甲基咪唑 、 四氮唑 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 lutidine 、 PyFNOP 、 硫化氢 、 叔丁胺 、 sodium iodide 作用下， 以 吡啶 、 甲苯 、 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

文献信息

• Solid phase synthesis of oligodeoxynucleoside phosphorodithioates by a phosphotriester method using a chemoselective coupling reagent
  作者：Jan Kehler、Ask Püschl、Otto Dahl

  DOI：10.1016/0040-4039(96)01820-5

  日期：1996.10

  A phosphotriester method has been developed for solid phase synthesis of oligodeoxynucleoside phosphorodithioates. Couplings are performed by chemoselective oxygen activation of protected nucleoside dithiophosphate anions 1, 7, 8, 9 with 4-nitro-6-trifluoromethylbenzotriazol-1-yl-oxy-tris(pyrrolidine)-phosphonium hexafluorophosphate (PyFNOP). Under optimised conditions coupling yields are above 95%

  已经开发了磷酸三酯方法用于固相合成寡脱氧核苷二硫代磷酸酯。偶联通过化学选择性氧激活保护的核苷二硫代磷酸盐阴离子进行1，7，8，9与4-硝基-6- trifluoromethylbenzotriazol -1-基-氧基-三（吡咯烷）鏻六氟磷酸盐（PyFNOP）。在最佳条件下，偶联10-20分钟的收率可达95％以上，解封后的产品不含硫代磷酸酯污染（检出限为0.5％）。