(2R,3R)-2,3-Dihydroxy-2-methyl-butyric acid ethyl ester | 141783-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R,3R)-2,3-Dihydroxy-2-methyl-butyric acid ethyl ester
• 英文别名: ethyl (2R,3R)-2,3-dihydroxy-2-methylbutanoate
• CAS: 141783-55-3
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: SJEQJQKAINSHTJ-IYSWYEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-Dihydroxy-2-methyl-butyric acid ethyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (R)-ethyl acetolactate
  参考文献：
  名称：

  Erythroselective aldol condensation of amine Free 2-t-butyl-5-methyl-2-phenyl-1,3-dioxolan-4-one lithium enolate synthesis of the ethyl acetolactate enantiomers

  摘要：

  Generated by halogen metal exchange, the sterically hindered 2-t-butyl-5-methyl-2-phenyl -1,3-dioxolan-4-one lithium enolate reacts in an erythroselective way with acetaldehyde. Separation of the resulting diastereomers, followed by alcoholysis lead to the corresponding enantiomerically pure diols.

  DOI：

  10.1016/s0040-4039(00)74171-2
• 作为产物：
  描述：

  (R)-2-tert-Butyl-5-(1-hydroxy-ethyl)-5-methyl-2-phenyl-[1,3]dioxolan-4-one 在 sodium ethanolate 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R)-2,3-Dihydroxy-2-methyl-butyric acid ethyl ester
  参考文献：
  名称：

  Erythroselective aldol condensation of amine Free 2-t-butyl-5-methyl-2-phenyl-1,3-dioxolan-4-one lithium enolate synthesis of the ethyl acetolactate enantiomers

  摘要：

  Generated by halogen metal exchange, the sterically hindered 2-t-butyl-5-methyl-2-phenyl -1,3-dioxolan-4-one lithium enolate reacts in an erythroselective way with acetaldehyde. Separation of the resulting diastereomers, followed by alcoholysis lead to the corresponding enantiomerically pure diols.

  DOI：

  10.1016/s0040-4039(00)74171-2

文献信息

• Baker’s yeast reduction of α-alkyl-α-hydroxy-β-keto esters
  作者：Didier Buisson、Xavier Baucherel、Eric Levoirier、Sylvain Juge

  DOI：10.1016/s0040-4039(99)02274-1

  日期：2000.2

  Cyclic or acyclic α-alkyl-α-hydroxy-β-keto esters were reduced by baker’s yeast with high stereospecificity. In the former case, one enantiomer of the racemic mixture was transformed into optically active trans-dihydroxy compounds, while the remaining α-hydroxy-β-keto ester was enantiopure.

  环状酵母或无环α-烷基-α-羟基-β-酮酸酯被具有高立体特异性的面包酵母还原。在前一种情况下，外消旋混合物的一种对映异构体被转化为旋光的反式-二羟基化合物，而其余的α-羟基-β-酮酸酯是对映体纯的。