[(2R,3S,5R)-2-[[2-anilinoethoxy(oxido)phosphaniumyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate | 1399820-01-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3S,5R)-2-[[2-anilinoethoxy(oxido)phosphaniumyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 1399820-01-9
• 化学式: C₂₀H₂₆N₃O₈P
• 分子量: 467.415
• InChiKey: KJOGHWDBZBGIOO-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[2-anilinoethoxy(oxido)phosphaniumyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate 在 碘 作用下， 以 乙腈 为溶剂， 生成 、
  参考文献：
  名称：

  Oxidation of H-Phosphonates with Iodine by Intramolecular Support of a 2-Pyridyl Thermolabile Protecting Group

  摘要：

  Acceleration of H-phosphonate diester oxidation with iodine accompanied by a thermolabile protecting group (TPG) is presented. It is shown that the intermediate product of this reaction is an oxazaphospholidine oxide which forms a phosphate diester only when a 2-pyridyl TPG is applied. The intermediate product is formed with exocyclic nitrogen. The absolute configurations of phosphorothioate diesters, H-phosphonate diesters, and oxazaphospholidine oxides were determined. P-31 NMR spectroscopy was used to evaluate the relationship between chemical shift and absolute configuration at the phosphorus center of H-phosphonate diesters and oxazaphospholidine oxides.

  DOI：

  10.1021/jo300937k
• 作为产物：
  描述：

  [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[(3-phenyl-1,3,2-oxazaphospholidin-2-yl)oxymethyl]oxolan-3-yl] acetate 在 二氯乙酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(2R,3S,5R)-2-[[2-anilinoethoxy(oxido)phosphaniumyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate 、 [(2R,3S,5R)-2-[[2-anilinoethoxy(oxido)phosphaniumyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
  参考文献：
  名称：

  Oxidation of H-Phosphonates with Iodine by Intramolecular Support of a 2-Pyridyl Thermolabile Protecting Group

  摘要：

  Acceleration of H-phosphonate diester oxidation with iodine accompanied by a thermolabile protecting group (TPG) is presented. It is shown that the intermediate product of this reaction is an oxazaphospholidine oxide which forms a phosphate diester only when a 2-pyridyl TPG is applied. The intermediate product is formed with exocyclic nitrogen. The absolute configurations of phosphorothioate diesters, H-phosphonate diesters, and oxazaphospholidine oxides were determined. P-31 NMR spectroscopy was used to evaluate the relationship between chemical shift and absolute configuration at the phosphorus center of H-phosphonate diesters and oxazaphospholidine oxides.

  DOI：

  10.1021/jo300937k