5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl N-butylphosphonamidate | 157793-53-8

• 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: 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl N-butylphosphonamidate
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(butylaminophosphonoyloxy)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 157793-53-8
• 化学式: C₃₅H₄₂N₃O₈P
• 分子量: 663.708
• InChiKey: KSWQZAAVRPEAMH-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  正丁胺 、 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl N-butylphosphonamidate 反应 70.0h， 生成 dibutylphosphoniamidate
  参考文献：
  名称：

  Sobkowski, Michal; Stawinski, Jacek; Sobkowska, Anna, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1803 - 1808

  摘要：

  DOI：
• 作为产物：
  描述：

  5'-O-dimethoxytritylthymidine 3'-H-phosphonate 在 三甲基乙酰氯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl N-butylphosphonamidate
  参考文献：
  名称：

  Aryl H-Phosphonates. 6. Synthetic Studies on the Preparation of Nucleoside N-Alkyl-H-phosphonamidates

  摘要：

  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.

  DOI：

  10.1021/jo962224z

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