[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyl 2,2-dimethylpropanoate | 135704-44-8

• 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]oxyphosphonoyl 2,2-dimethylpropanoate
• CAS: 135704-44-8
• 化学式: C₃₆H₄₁N₂O₁₀P
• 分子量: 692.703
• InChiKey: IUJCHEUUHHKJCD-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  139
• 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]oxyphosphonoyl 2,2-dimethylpropanoate 在 硫化氢 作用下， 以 1,4-二氧六环 为溶剂， 生成 5'-O-dimethoxytritylthymidin-3'-yl trimethylsilyl H-phosphonothioate
  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：

  三甲基乙酰氯 、 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 在 喹啉 作用下， 以 乙腈 为溶剂， 生成 [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Conversion of Nucleoside H-Phosphonate Monoesters to the Corresponding H-Phosphonothioates. 31P NMR Studies

  摘要：

  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.

  DOI：

  10.1080/15257779508012455

文献信息

• Nucleoside H-Phosphonates, XXII: Synthesis and Properties of New Nucleotide Analogues - H-Phosphonothiolate Diesters
  作者：Jacek Stawinski、Renata Hiresova

  DOI：10.1055/s-2007-991072

  日期：——

  Nucleoside H-phosphonates, XXII: Synthesis and properties of new nucleotide analogues - H-phosphonothiolate diesters

  核苷 H-膦酸酯，XXII：新核苷酸类似物的合成和性质 - H-硫代膦酸二酯
• Aryl <i>H</i>-Phosphonates. 6. Synthetic Studies on the Preparation of Nucleoside <i>N</i>-Alkyl-<i>H</i>-phosphonamidates
  作者：Anna Sobkowska、Michał Sobkowski、Jacek Cieślak、Adam Kraszewski、Inger Kers、Jacek Stawiński

  DOI：10.1021/jo962224z

  日期：1997.7.1

  Various approaches to the synthesis of nucleoside H-phosphonamidates have been investigated. Direct couplings of nucleoside H-phosphonates with amines have been hampered by extensive reactions of the condensing agents with amines. Preactivation of nucleoside H-phosphonates with pivaloyl chloride or chlorophosphates, followed by the addition of amines, notably diminished these side reactions. The most efficient and versatile route to nucleoside N-alkyl H-phosphonates was found to be aminolysis of the in situ-produced aryl nucleoside H-phosphonates with appropriate amines.
• STAWINSKI, JACEK;STROMBERG, ROGER;ZAIN, RULA, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 515-516
  作者：STAWINSKI, JACEK、STROMBERG, ROGER、ZAIN, RULA

  DOI：——

  日期：——