methyl 4-bromo-5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(oxan-2-yl)pyrazole-3-carboxylate | 190263-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 4-bromo-5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(oxan-2-yl)pyrazole-3-carboxylate
• CAS: 190263-34-4
• 化学式: C₁₅H₂₁BrN₂O₆
• 分子量: 405.246
• InChiKey: OJWWVNQBZFVSKF-JSBCTHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  103.04
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 4-bromo-5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(oxan-2-yl)pyrazole-3-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以85%的产率得到4-Bromo-5-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-(tetrahydro-pyran-2-yl)-2H-pyrazole-3-carboxylic acid amide
  参考文献：
  名称：

  4-Substituted-5(3)-carbamoyl-3(5)-(2-deoxy-β-D-ribofuranosyl)pyrazoles. Application of Palladium Catalyzed Glycal Coupling Methodology to the Synthesis of Pyrazofurin Analogs

  摘要：

  Analogs of the C-nucleoside pyrazofurin were prepared in 7-9 steps using a key Pd(0)-catalyzed coupling reaction between protected iodopyrazoles 6a and 6b and glycal 8 to form the glycosyl bond. Conditions for this reaction were improved from those previously described for related reactions in order to maximize product yields and eliminate the need for triphenylarsine.

  DOI：

  10.1080/07328319708001352
• 作为产物：
  描述：

  methyl 4-bromo-5-iodo-2-(oxan-2-yl)pyrazole-3-carboxylate 在 四丁基氟化铵 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 、 三(邻甲基苯基)磷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 15.42h， 生成 methyl 4-bromo-5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(oxan-2-yl)pyrazole-3-carboxylate
  参考文献：
  名称：

  4-Substituted-5(3)-carbamoyl-3(5)-(2-deoxy-β-D-ribofuranosyl)pyrazoles. Application of Palladium Catalyzed Glycal Coupling Methodology to the Synthesis of Pyrazofurin Analogs

  摘要：

  Analogs of the C-nucleoside pyrazofurin were prepared in 7-9 steps using a key Pd(0)-catalyzed coupling reaction between protected iodopyrazoles 6a and 6b and glycal 8 to form the glycosyl bond. Conditions for this reaction were improved from those previously described for related reactions in order to maximize product yields and eliminate the need for triphenylarsine.

  DOI：

  10.1080/07328319708001352