(3R^*,5R^*)-Methyl 3,5-Dihydroxy-7-phenylheptanoate | 107400-61-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R^*,5R^*)-Methyl 3,5-Dihydroxy-7-phenylheptanoate
• 英文别名: methyl (3S,5S)-3,5-dihydroxy-7-phenylheptanoate
• CAS: 107400-61-3；107400-62-4；133833-20-2
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: CRLBHHHQWUGRFO-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R^*,5R^*)-Methyl 3,5-Dihydroxy-7-phenylheptanoate 在 porcine pancreatic lipase 作用下， 以 乙醚 为溶剂， 反应 96.0h， 以35%的产率得到(4R,6R)-6-(2-cyclohexylethyl)-4-hydroxytetrahydropyran-2-one
  参考文献：
  名称：

  A remarkable short synthesis of optically active mevinic acid analogs by biocatalytic lactonization of syn-3,5-dihydroxy esters

  摘要：

  DOI：

  10.1021/jo00012a047
• 作为产物：
  描述：

  Methyl 5-hydroxy-3-oxo-7-phenylheptanoate 在 titanium(IV) isopropylate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (3R^*,5R^*)-Methyl 3,5-Dihydroxy-7-phenylheptanoate
  参考文献：
  名称：

  A remarkable short synthesis of optically active mevinic acid analogs by biocatalytic lactonization of syn-3,5-dihydroxy esters

  摘要：

  DOI：

  10.1021/jo00012a047

文献信息

• Diastereoselective synthesis of protected syn 1,3-diols by base-catalyzed intramolecular conjugate addition of hemiacetal-derived alkoxide nucleophiles
  作者：David A. Evans、Joelle A. Gauchet-Prunet

  DOI：10.1021/jo00061a018

  日期：1993.4

  Reaction of the illustrated unsaturated hydroxy esters (X = OMe, R2 = H, Me) and amides (X = N(Me)OMe, R2 = H, Me) with benzaldehyde and potassium alkoxide or amide bases is reported. The resulting benzylidene acetals are obtained in good yields (71-84%) and with high selectivity (>90: 10). In addition to an exploration of the scope of the reaction, a mechanistic study, involving the use of deuterated benzaldehyde to ascertain the rate-determining step of the process, is described.
• Stereoselective Reduction of ?-Hydroxy-?-ketoesters
  作者：Faizulla G. Kathawala、Bernhard Prager、Kapa Prasad、Oljan Repi?、Michael J. Shapiro、Russell S. Stabler、Leo Widler

  DOI：10.1002/hlca.19860690407

  日期：1986.6.18

  AbstractThe reduction of δ‐hydroxy‐β‐ketoesters 1 was investigated with three different reducing agents. In several instances, high selectivity in favor of syn‐1,3‐diols was observed.
• A remarkable short synthesis of optically active mevinic acid analogs by biocatalytic lactonization of syn-3,5-dihydroxy esters
  作者：Carlo Bonini、Piero Pucci、Licia Viggiani

  DOI：10.1021/jo00012a047

  日期：1991.6