(2R,3S)-2,3-dihydroxy-2-methyl-pentanoic acid | 92691-47-9

• 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: (2R,3S)-2,3-dihydroxy-2-methyl-pentanoic acid
• 英文别名: (2R,3S)-2,3-dihydroxy-2-methylpentanoic acid；(2R,3S)-2-Methyl-2,3-dihydroxypentanoic acid
• CAS: 92691-47-9
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: WBPIKRWVCLNWOS-UJURSFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2R,3S)-2,3-dihydroxy-2-methyl-pentanoic acid 在 氯化亚砜 作用下， 反应 20.0h， 以0.12 g的产率得到methyl (2R,3S)-2,3-dihydroxy-2-methyl-pentanoate
  参考文献：
  名称：

  Synthesis and desilylation of (2R,3S)-α-methyl-α-silyl-α,β-2,3-dihydroxycarboxylic methyl esters

  摘要：

  Addition reactions of the chiral lithium (2S)-enolates of the (2S,5S)-2-tert-butyl-5,-methyl-[1,3]dioxolan-4-one and (2S,5S)-2-tert-butyl-2,5-dimethyl-[1,3]dioxolan-4-one with linear aliphatic acylsilanes yield the corresponding (2S,5R,1'R)-1'-trimethylsilyl-dioxolanone alcohols. Sodium methoxide-induced removal of the acetal center at C-2 affords the corresponding methyl (2R,3R)-2,3-dihydroxy-2-methyl-3-trimethylsilyl alkanoates. The desilylation of these esters occurs with complete retention of configuration yielding the corresponding (2R,3S)-2,3-dihydroxy-2-methyl-alkanoic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00440-8
• 作为产物：
  描述：

  (2S,5R,1'R)-2-tert-butyl-5-(1-hydroxy-1-trimethylsilanyl-ethyl)-2,5-dimethyl-1,3-dioxolan-4-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以70%的产率得到(2R,3S)-2,3-dihydroxy-2-methyl-pentanoic acid
  参考文献：
  名称：

  Synthesis and desilylation of (2R,3S)-α-methyl-α-silyl-α,β-2,3-dihydroxycarboxylic methyl esters

  摘要：

  Addition reactions of the chiral lithium (2S)-enolates of the (2S,5S)-2-tert-butyl-5,-methyl-[1,3]dioxolan-4-one and (2S,5S)-2-tert-butyl-2,5-dimethyl-[1,3]dioxolan-4-one with linear aliphatic acylsilanes yield the corresponding (2S,5R,1'R)-1'-trimethylsilyl-dioxolanone alcohols. Sodium methoxide-induced removal of the acetal center at C-2 affords the corresponding methyl (2R,3R)-2,3-dihydroxy-2-methyl-3-trimethylsilyl alkanoates. The desilylation of these esters occurs with complete retention of configuration yielding the corresponding (2R,3S)-2,3-dihydroxy-2-methyl-alkanoic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00440-8

文献信息

• (α-Alkylation of α-heterosubstituted carboxylic acids without racemization
  作者：Dieter Seebach、Reto Naef、Giorgio Calderari

  DOI：10.1016/s0040-4020(01)82417-0

  日期：1984.1

  α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-l,3-dioxolanones or 1,3-oxathiolanones (2); the predominate CK-isomers are separated by crystallization. The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid furnish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones

  将α-羟基和α-巯基羧酸与新戊醛缩合，生成2-叔丁基-5-取代的-1,3-二氧戊环酮或1,3-氧杂硫杂环戊酮（2）；主要的CK异构体通过结晶分离。的顺式二取代的杂环2从乳酸，扁桃酸和苹果酸配料衍生，用LDA，与亲电子试剂如烷基卤化物，醛和酮，去质子化反应后，水解α-α支链羟基-羧酸（3，6，8，9，10）。这些归因于质子在α-CO位置上的整体置换而保留了构型。旋光羧酸是α-烷基化的，没有消旋作用，也没有使用手性助剂（“手性的自我复制”方案I）。非对映选择性（ds）通常> 95％（表1、2和20-25）。
• 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。
• HEATHCOCK C. H.; YOUNG S. D.; HAGEN J. P.; PIRRING M. C.; WHITE C. T.; VA+, J. ORG. CHEM., 1980, 45, NO 19, 3846-3856
  作者：HEATHCOCK C. H.、 YOUNG S. D.、 HAGEN J. P.、 PIRRING M. C.、 WHITE C. T.、 VA+

  DOI：——

  日期：——
• SEEBACH, D.;NAEF, R.;CALDERARI, G., TETRAHEDRON, 1984, 40, N 8, 1313-1324
  作者：SEEBACH, D.、NAEF, R.、CALDERARI, G.

  DOI：——

  日期：——
• Synthesis and desilylation of (2R,3S)-α-methyl-α-silyl-α,β-2,3-dihydroxycarboxylic methyl esters
  作者：Arturo Battaglia、Eleonora Baldelli、Gaetano Barbaro、Patrizia Giorgianni、Andrea Guerrini、Magda Monari、Simona Selva

  DOI：10.1016/s0957-4166(02)00440-8

  日期：2002.8

  Addition reactions of the chiral lithium (2S)-enolates of the (2S,5S)-2-tert-butyl-5,-methyl-[1,3]dioxolan-4-one and (2S,5S)-2-tert-butyl-2,5-dimethyl-[1,3]dioxolan-4-one with linear aliphatic acylsilanes yield the corresponding (2S,5R,1'R)-1'-trimethylsilyl-dioxolanone alcohols. Sodium methoxide-induced removal of the acetal center at C-2 affords the corresponding methyl (2R,3R)-2,3-dihydroxy-2-methyl-3-trimethylsilyl alkanoates. The desilylation of these esters occurs with complete retention of configuration yielding the corresponding (2R,3S)-2,3-dihydroxy-2-methyl-alkanoic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.