[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[oxido(pyridin-2-ylmethoxy)phosphaniumyl]oxymethyl]oxolan-3-yl] acetate | 1399820-12-2

• 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)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[oxido(pyridin-2-ylmethoxy)phosphaniumyl]oxymethyl]oxolan-3-yl] acetate
• CAS: 1399820-12-2
• 化学式: C₁₈H₂₂N₃O₈P
• 分子量: 439.362
• InChiKey: SOYVCYUISNRCPR-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-吡啶甲醇 、 3'-O-acetylthymidine-5'-O-H-phosphonate 在 吡啶 、 氯磷酸二苯酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[oxido(pyridin-2-ylmethoxy)phosphaniumyl]oxymethyl]oxolan-3-yl] acetate 、 [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[oxido(pyridin-2-ylmethoxy)phosphaniumyl]oxymethyl]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

文献信息

• Oxidation of H-Phosphonates with Iodine by Intramolecular Support of a 2-Pyridyl Thermolabile Protecting Group
  作者：Tomasz Ratajczak、Marcin K. Chmielewski

  DOI：10.1021/jo300937k

  日期：2012.9.21

  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.