[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-trimethylsilyloxyphosphanyl] 2,2-dimethylpropanoate | 135704-45-9

• 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-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-trimethylsilyloxyphosphanyl] 2,2-dimethylpropanoate
• CAS: 135704-45-9
• 化学式: C₃₉H₄₉N₂O₁₀PSi
• 分子量: 764.885
• InChiKey: HJKXTAIQFKQXMH-MPYYKDOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-trimethylsilyloxyphosphanyl] 2,2-dimethylpropanoate 在 硫化氢 、 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 5'-O-(4,4-dimethoxytrityl)thymidin-3'-yl H-phosphonothioate, triethylammonium salt
  参考文献：
  名称：

  Nucleoside H-Phosphonates. 15. Preparation of Nucleoside H-Phosphonothioate Monoesters from the Corresponding Nucleoside H-Phosphonates

  摘要：

  A convenient method for the preparation of nucleoside 3'-H-phosphonothioate monoesters from suitably protected nucleoside 3'-H-phosphonates has been developed. It consists of activation of nucleoside H-phosphonates with pivaloyl chloride in the presence of a limited amount of a base followed by treatment with 1,1,1,3,3,3-hexamethyldisilathiane (HMDST).

  DOI：

  10.1021/jo00130a025
• 作为产物：
  描述：

  triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 在 喹啉 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.08h， 生成 [[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-trimethylsilyloxyphosphanyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Nucleoside H-Phosphonates. 15. Preparation of Nucleoside H-Phosphonothioate Monoesters from the Corresponding Nucleoside H-Phosphonates

  摘要：

  A convenient method for the preparation of nucleoside 3'-H-phosphonothioate monoesters from suitably protected nucleoside 3'-H-phosphonates has been developed. It consists of activation of nucleoside H-phosphonates with pivaloyl chloride in the presence of a limited amount of a base followed by treatment with 1,1,1,3,3,3-hexamethyldisilathiane (HMDST).

  DOI：

  10.1021/jo00130a025

文献信息

• Conversion of Nucleoside H-Phosphonate Monoesters to the Corresponding H-Phosphonothioates. 31P NMR Studies
  作者：Jacek Stawinski、Rula Zain

  DOI：10.1080/15257779508012455

  日期：1995.5.1

  P-31 NMR Studies on the conversion of nucleoside H-phosphonate monoesters into the corresponding H-phosphonothioates revealed that the key intermediate, the nucleoside trimethylsilyl pivaloyl phosphite 3, may undergo under the reaction conditions at least two parallel transformations to, most likely, the nucleoside trimethylsilyl chlorophosphite 6 and the monosilylated nucleoside H-phosphonate 5.
• Nucleoside H-Phosphonates. 15. Preparation of Nucleoside H-Phosphonothioate Monoesters from the Corresponding Nucleoside H-Phosphonates
  作者：Rula Zain、Roger Stroemberg、Jacek Stawinski

  DOI：10.1021/jo00130a025

  日期：1995.12

  A convenient method for the preparation of nucleoside 3'-H-phosphonothioate monoesters from suitably protected nucleoside 3'-H-phosphonates has been developed. It consists of activation of nucleoside H-phosphonates with pivaloyl chloride in the presence of a limited amount of a base followed by treatment with 1,1,1,3,3,3-hexamethyldisilathiane (HMDST).