(2S,3S) ethyl 2,3-dihydroxy-2-methylbutanoate | 141783-54-2

• 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: (2S,3S) ethyl 2,3-dihydroxy-2-methylbutanoate
• 英文别名: Ethyl (2S,3S)-2-methyl-2,3-dihydroxybutanoate；ethyl (2S,3S)-2,3-dihydroxy-2-methylbutanoate
• CAS: 141783-54-2
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: SJEQJQKAINSHTJ-FSPLSTOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (2S,3S) ethyl 2,3-dihydroxy-2-methylbutanoate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (S)-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：

  (2S,3S)-3-Benzyloxy-2-hydroxy-2-methyl-butyric acid 在 palladium dihydroxide 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 (2S,3S) ethyl 2,3-dihydroxy-2-methylbutanoate
  参考文献：
  名称：

  Carda, Miguel; Falomir, Eva; Murga, Juan, Journal of Chemical Research, Miniprint, 1996, # 1, p. 201 - 205

  摘要：

  DOI：

文献信息

• Addition Reactions of Aldehydes to Lithium Enolates of 1,3-Dioxolan-4-ones: A Configurational Reassessment
  作者：Arturo Battaglia、Gaetano Barbaro、Patrizia Giorgianni、Andrea Guerrini、Carlo Bertucci、Silvano Geremia

  DOI：10.1002/1521-3765(20001002)6:19<3551::aid-chem3551>3.0.co;2-r

  日期：2000.10.2

  The results for the addition reactions of chiral lithium (2S)-enolates of 1,3-dioxolan-4-ones to aldehydes and to acetophenone, yielding the corresponding dioxolanone alcohols have been revised. The results reported herein differ from those reported in the literature, both in product distribution and in the stereochemical assignment of the products. In fact, in several cases no stereocontrol was observed

  修订了1,3-二氧戊环-4-酮手性锂（2S）-烯酸酯与醛和对乙酰苯的加成反应，生成相应的二氧戊环醇的结果。本文报道的结果在产物分布和产物的立体化学分配上均不同于文献报道的结果。实际上，在几种情况下，在烯醇锂的C5碳原子上未观察到立体控制。还对几种二氧戊环醇进行了（2S，5R，1'S）/（2S，5R，1'R）立体化学评估。主要构象体被认为具有分子内氢键合的五元环结构，而不是先前对于环状二氧戊环醇所建议的六元环结构。
• 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。
• 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
  作者：Alfred Greiner、Jean-Yves Ortholand

  DOI：10.1016/s0040-4039(00)74171-2

  日期：1992.3

  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.
• Carda, Miguel; Falomir, Eva; Murga, Juan, Journal of Chemical Research, Miniprint, 1996, # 1, p. 201 - 205
  作者：Carda, Miguel、Falomir, Eva、Murga, Juan、Marco, J. Alberto

  DOI：——

  日期：——