(2S,3R)-3-Hydroxy-2,4-dimethyl-pentanoic acid phenyl ester | 144408-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (2S,3R)-3-Hydroxy-2,4-dimethyl-pentanoic acid phenyl ester
• 英文别名: phenyl (2S,3R)-3-hydroxy-2,4-dimethylpentanoate
• CAS: 144408-67-3
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: DWPIPHDJGDDYKF-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-Phenoxy-1-(trimethylsiloxy)propen 、 异丁醛 在 chiral borane complex I 、 四丁基氟化铵 作用下， 生成 (2S,3R)-3-Hydroxy-2,4-dimethyl-pentanoic acid phenyl ester 、 anti-phenyl 3-hydroxy-2,4-dimethylpentanoate
  参考文献：
  名称：

  在手性硼烷配合物的存在下，甲硅烷基乙烯酮缩醛与醛的催化不对称醛醇缩合反应。硝基乙烷作为催化条件下的高效溶剂

  摘要：

  由（S）-缬氨酸的对硝基苯磺酰胺和BH 3 ·THF配合物原位制备的手性硼烷试剂在20摩尔％的存在下，硅酮烯酮缩醛与醛的催化不对称醛醇缩醛反应，得到β-羟基羧酸在使用硝基乙烷作为有效溶剂的条件下，该酯具有良好的化学收率以及出色的对映选择性。

  DOI：

  10.1016/s0040-4039(00)61236-4

文献信息

• A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions
  作者：Syun-ichi Kiyooka、Mostofa A. Hena

  DOI：10.1021/jo990342r

  日期：1999.7.1

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).
• The catalytic asymmetric aldol reaction of silyl ketene acetals with aldehydes in the presence of a chiral borane complex. Nitroethane as a highly effective solvent for catalytic conditions
  作者：Syun-ichi Kiyooka、Yuichi Kaneko、Ken-ichi Kume

  DOI：10.1016/s0040-4039(00)61236-4

  日期：1992.8

  Catalytic asymmetric aldol reactions of silyl ketene acetals with aldehydes in the presence of 20 mol % of the chiral borane reagent, prepared in situ from the p-nitrobenzenesulfonamide of (S)-valine and BH3·THF complex, gave β-hydroxy carboxylic acid esters in good chemical yields along with excellent enantioselectivity under conditions that employ nitroethane as an effective solvent.

  由（S）-缬氨酸的对硝基苯磺酰胺和BH 3 ·THF配合物原位制备的手性硼烷试剂在20摩尔％的存在下，硅酮烯酮缩醛与醛的催化不对称醛醇缩醛反应，得到β-羟基羧酸在使用硝基乙烷作为有效溶剂的条件下，该酯具有良好的化学收率以及出色的对映选择性。