[(2R,3R,4R,5R)-4-benzoyloxy-2-[[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-3-yl]oxyphosphinothioyloxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate | 135257-72-6

• 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: [(2R,3R,4R,5R)-4-benzoyloxy-2-[[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-3-yl]oxyphosphinothioyloxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate
• CAS: 135257-72-6
• 化学式: C₅₈H₆₁N₄O₁₅PSSi
• 分子量: 1145.27
• InChiKey: KTHQPYHNYGNVNZ-IENOKORUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  80
• 可旋转键数：
  23
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  248
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-4-benzoyloxy-2-[[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-3-yl]oxyphosphinothioyloxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate 在 3H-1,2-苯并二硫醇-3-酮 作用下， 以 吡啶 、 水 为溶剂， 以100%的产率得到[(2R,3R,4R,5R)-4-benzoyloxy-2-[[[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-3-yl]oxy-sulfanylphosphinothioyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate
  参考文献：
  名称：

  Nucleoside H-phosphonates. 13. Studies on 3H-1,2-benzodithiol-3-one derivatives as sulfurizing reagents for H-phosphonate and H-phosphonothioate diesters

  摘要：

  Formation of O-oxidized products during sulfurization of H-phosphonothioate and H-phosphonate diesters with 3H-1,2-benzodithiol-3-one 1,1-dioxide (1) was found to be due to generation of the O-oxidizing agents, most likely 3H-2,1-benzoxathiol-3-one 1-oxide (4) and 3H-2,1-benzoxathiol-3-one (5), during the course of the reactions. Another source of the side products formation may be the disproportionation of 1 that occurs in the presence of triethylamine. To overcome these problems, a new sulfur-transferring reagent, 3H-1,2-benzodithiol-3-one (3), has been developed. Under aqueous reaction conditions, which are compatible with both solution- and solid-phase synthesis of oligonucleotides, the reagent 3 furnished clean and fast conversion of H-phosphonothioate and H-phosphonate diesters into the corresponding phosphorodi- and phosphoromonothioates.

  DOI：

  10.1021/jo00017a033