5'-O-(4-Monomethoxytrityl)-2'-desoxythymidin-3'-O-hydrogenphosphonat | 56883-48-8

• 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-Monomethoxytrityl)-2'-desoxythymidin-3'-O-hydrogenphosphonat
• 英文别名: 5'-O-monomethoxytritylthymidine 3'-H-phosphonate；5'-O-(p-Monomethoxytrityl)thymidin-3'-phosphit；O^3'-hydroxyphosphinoyl-O^5'-(4-methoxy-trityl)-thymidine
• CAS: 56883-48-8
• 化学式: C₃₀H₃₁N₂O₈P
• 分子量: 578.558
• InChiKey: RMHQOTMIDCQXEC-NODVFIEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129.08
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4-Monomethoxytrityl)-2'-desoxythymidin-3'-O-hydrogenphosphonat 在 吡啶 、 碘 、 三甲基乙酰氯 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Stereospecific oxidation and oxidative coupling of H-phosphonate and H-phosphonothioate diesters

  摘要：

  Oxidation of dinucleoside H-phosphonothioate diesters with the aid of iodine in aqueous acetonitrile and triethylamine, and oxidative coupling of H-phosphonate and H-phosphonothioate diesters with ethanol under similar conditions in anhydrous acetonitrile were found to be stereospecific reactions.

  DOI：

  10.1016/s0040-4039(00)79847-9

文献信息

• Schott, Herbert; Haeussler, Markus P.; Schwendener, Reto A., Liebigs Annalen der Chemie, 1994, # 3, p. 277 - 282
  作者：Schott, Herbert、Haeussler, Markus P.、Schwendener, Reto A.

  DOI：——

  日期：——
• Nucleoside H-phosphonates. 14. Synthesis of nucleoside phosphoroselenoates and phosphorothioselenoates via stereospecific selenization of the corresponding H-phosphonate and H-phosphonothioate diesters with the aid of new selenium-transfer reagent, 3H-1,2-benzothiaselenol-3-one
  作者：Jacek Stawinski、Mats Thelin

  DOI：10.1021/jo00080a021

  日期：1994.1

  An efficient conversion of nucleoside H-phosphonate and nucleoside H-phosphonothioate diesters into the corresponding phosphoroselenoates and phosphorothioselenoates was achieved with a new selenium-transferring reagent, 3M-1,2-benzothiaselenol-3-one (BTSe, 1). The reagent is soluble in common organic solvents and shows an enhanced rate of selenium transfer compared to elemental selenium or potassium selenocyanate. The reaction was found to be stereospecific and occurs with retention of configuration at the phosphorus center. BTSe also proved to be effective in the conversion of phosphite triesters into the corresponding phosphoroselenoates under reactions conditions which are compatible with both solution- and solid-phase synthesis of oligonucleotides.