ethyl (5R*,6S*)-5-ethoxycarbonyl-6-hydroxyheptanoate

• 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: ethyl (5R*,6S*)-5-ethoxycarbonyl-6-hydroxyheptanoate
• 英文别名: diethyl (2R)-2-[(1S)-1-hydroxyethyl]hexanedioate
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: RBHKJDHDDPSQTE-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 在 cerium(III) chloride 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 ethyl (5R*,6S*)-5-ethoxycarbonyl-6-hydroxyheptanoate 、 ethyl (5R*,6R*)-5-ethoxycarbonyl-6-hydroxyheptanoate
  参考文献：
  名称：

  Reversed Stereochemical Control in the Presence of CeCl₃ and TiCl₄ in the Lewis Acid Mediated Reduction of α-Alkyl-β-keto Esters by Metal Hydrides. A General Methodology for the Diastereoselective Synthesis of syn- and anti-α-Alkyl-β-hydroxy Esters

  摘要：

  The Lewis acid-mediated reduction of alpha-alkyl-beta-keto esters has been shown to proceed by different stereochemical control depending on the nature of the metal atom. Strongly chelating TiCl4 led to the syn isomer in high diastereomeric excess in noncoordinating solvents (CH2Cl2) at -78 degrees C with BH3. py as reducing agent, while nonchelating CeCl3 gave a high excess of the anti isomer in coordinating solvents (THF) at the same temperature with lithium triethylborohydride (LiEt3BH) as reducing agent. The methodology has been successfully utilized for obtaining important syn- and anti-alpha-alkyl-beta-hydroxy esters with high diastereoselectivity.

  DOI：

  10.1021/jo9821574

文献信息

• Reversed Stereochemical Control in the Presence of CeCl₃ and TiCl₄ in the Lewis Acid Mediated Reduction of α-Alkyl-β-keto Esters by Metal Hydrides. A General Methodology for the Diastereoselective Synthesis of <i>s</i><i>yn</i>- and <i>a</i><i>nti</i>-α-Alkyl-β-hydroxy Esters
  作者：Enrico Marcantoni、Sara Alessandrini、Marco Malavolta、Giuseppe Bartoli、Maria Cristina Bellucci、Letizia Sambri、Renato Dalpozzo

  DOI：10.1021/jo9821574

  日期：1999.3.1

  The Lewis acid-mediated reduction of alpha-alkyl-beta-keto esters has been shown to proceed by different stereochemical control depending on the nature of the metal atom. Strongly chelating TiCl4 led to the syn isomer in high diastereomeric excess in noncoordinating solvents (CH2Cl2) at -78 degrees C with BH3. py as reducing agent, while nonchelating CeCl3 gave a high excess of the anti isomer in coordinating solvents (THF) at the same temperature with lithium triethylborohydride (LiEt3BH) as reducing agent. The methodology has been successfully utilized for obtaining important syn- and anti-alpha-alkyl-beta-hydroxy esters with high diastereoselectivity.