[(4R)-2-(acetyloxymethyl)-4-(2,4-difluorophenyl)-4-hydroxy-5-(1,2,4-triazol-1-yl)pentyl] acetate | 195509-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(4R)-2-(acetyloxymethyl)-4-(2,4-difluorophenyl)-4-hydroxy-5-(1,2,4-triazol-1-yl)pentyl] acetate
• CAS: 195509-45-6
• 化学式: C₁₈H₂₁F₂N₃O₅
• 分子量: 397.379
• InChiKey: XGSGMPQQWVWWMM-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(4R)-2-(acetyloxymethyl)-4-(2,4-difluorophenyl)-4-hydroxy-5-(1,2,4-triazol-1-yl)pentyl] acetate 在 Amano Lipase AK (Pseudomonas sp.) 、 potassium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以17%的产率得到(4R)-4-(2,4-difluorophenyl)-2-(hydroxymethyl)-5-(1,2,4-triazol-1-yl)pentane-1,4-diol
  参考文献：
  名称：

  Enzymatic Desymmetrization of Prochiral 2-Substituted-1,3-propanediols:  A Practical Chemoenzymatic Synthesis of a Key Precursor of SCH51048, a Broad-Spectrum Orally Active Antifungal Agent

  摘要：

  Two examples of a practical enzymatic desymmetrization of a 2-substituted-1,3-propanediol and their application to the synthesis of SCH51048, a broad-spectrum orally active antifungal, are described. In each case, enzymatic catalysis under both hydrolytic and transesterification conditions is described. In the first example the key intermediate, the R,S-monoester of triol 6, was obtained via Amano Lipase AK catalyzed hydrolysis of the dibutyrate 11b, or Novo SP435 catalyzed acetylation of triol 6. In the second example, desymmetrization of diol 13a using Novo SP435 or of dibutyrate 13c using Amano Lipase CE furnished the S-monoester (S)-14b,c, a key intermediate ;in a new efficient synthesis of SCH51048. Optimization of the Novo SP435 acetylation of diol 13a and the scaleup of the reaction is also described.

  DOI：

  10.1021/jo9709920
• 作为产物：
  描述：

  在 Amano Lipase AK (Pseudomonas sp.) 、 potassium chloride 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 [(4R)-2-(acetyloxymethyl)-4-(2,4-difluorophenyl)-4-hydroxy-5-(1,2,4-triazol-1-yl)pentyl] acetate
  参考文献：
  名称：

  Enzymatic Desymmetrization of Prochiral 2-Substituted-1,3-propanediols:  A Practical Chemoenzymatic Synthesis of a Key Precursor of SCH51048, a Broad-Spectrum Orally Active Antifungal Agent

  摘要：

  Two examples of a practical enzymatic desymmetrization of a 2-substituted-1,3-propanediol and their application to the synthesis of SCH51048, a broad-spectrum orally active antifungal, are described. In each case, enzymatic catalysis under both hydrolytic and transesterification conditions is described. In the first example the key intermediate, the R,S-monoester of triol 6, was obtained via Amano Lipase AK catalyzed hydrolysis of the dibutyrate 11b, or Novo SP435 catalyzed acetylation of triol 6. In the second example, desymmetrization of diol 13a using Novo SP435 or of dibutyrate 13c using Amano Lipase CE furnished the S-monoester (S)-14b,c, a key intermediate ;in a new efficient synthesis of SCH51048. Optimization of the Novo SP435 acetylation of diol 13a and the scaleup of the reaction is also described.

  DOI：

  10.1021/jo9709920