[(2R,4R)-4-(2,4-difluorophenyl)-4-hydroxy-2-(hydroxymethyl)-5-(1,2,4-triazol-1-yl)pentyl] acetate | 149809-50-7

• 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: [(2R,4R)-4-(2,4-difluorophenyl)-4-hydroxy-2-(hydroxymethyl)-5-(1,2,4-triazol-1-yl)pentyl] acetate
• CAS: 149809-50-7
• 化学式: C₁₆H₁₉F₂N₃O₄
• 分子量: 355.341
• InChiKey: FSSIOGWQMACGQL-WBMJQRKESA-N

物化性质

• 沸点：
  554.0±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  97.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,4R)-4-(2,4-difluorophenyl)-4-hydroxy-2-(hydroxymethyl)-5-(1,2,4-triazol-1-yl)pentyl] acetate 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (2S,4R)-4-(2,4-difluorophenyl)-2-(oxan-2-yloxymethyl)-5-(1,2,4-triazol-1-yl)pentane-1,4-diol
  参考文献：
  名称：

  具有远程手性功能的PPL催化的2-取代的前手性1,3-二醇的酶促不对称化：对SCH 45012 eutomer的合成的改进

  摘要：

  猪胰脂肪酶（PPL）催化已用于建立顺式（四氢呋喃基甲基）甲苯磺酸4的两个立体中心。除了对2的手性1,3-二醇片段的羟基进行酶促区分外，外消旋二醇10的成功酶解提供了通往重要前体1的另一条途径。

  DOI：

  10.1016/0040-4039(94)88071-9
• 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 [(2R,4R)-4-(2,4-difluorophenyl)-4-hydroxy-2-(hydroxymethyl)-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

文献信息

• 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
  作者：Brian Morgan、David R. Dodds、Aleksey Zaks、David R. Andrews、Ricardo Klesse

  DOI：10.1021/jo9709920

  日期：1997.10.1

  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.
• PPL-catalyzed enzymatic asymmetrization of a 2-substituted prochiral 1,3-diol with remote chiral functionality: Improvements toward synthesis of the eutomers of SCH 45012
  作者：Raymond G. Lovey、Anil K. Saksena、Viyyoor M. Girijavallabhan

  DOI：10.1016/0040-4039(94)88071-9

  日期：1994.8

  pancreatic lipase (PPL) catalysis has been used to establish both stereocenters of the cis-(tetrahydrofuranylmethy) tosylate 4. In addition to the enzymatic differentiation of the hydroxyl groups of the pro-chiral 1,3-diol segment of 2, successful enzymatic resolution of the racemic diol 10 provided an alternate route to the important precursor 1.

  猪胰脂肪酶（PPL）催化已用于建立顺式（四氢呋喃基甲基）甲苯磺酸4的两个立体中心。除了对2的手性1,3-二醇片段的羟基进行酶促区分外，外消旋二醇10的成功酶解提供了通往重要前体1的另一条途径。