(2S)-2-Hydroxypentanoic acid methyl ester | 95912-79-1

• 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: (2S)-2-Hydroxypentanoic acid methyl ester
• 英文别名: (S)-2-Hydroxypentansaeuremethylester；(2S)-methyl 2-hydroxy-pentanoate；(S)-methyl 2-hydroxypentanoate；methyl (S)-2-hydroxypentanoate；(S)-methyl 2-hydroxyvalerate；(S)-2-hydroxy-valeric acid methyl ester；methyl (2S)-2-hydroxypentanoate
• CAS: 95912-79-1
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: QCZPJJIXHJSOMY-YFKPBYRVSA-N

物化性质

• 沸点：
  174.2±8.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-Hydroxypentanoic acid methyl ester 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-2-[2]naphthyloxy-valeric acid
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling Investigation of New Chiral Fibrates with PPARα and PPARγ Agonist Activity

  摘要：

  Peroxisome proliferator-activated receptors (PPARs) are ligand-activated transcription factors that govern lipid and glucose homeostasis playing a central role in cardiovascular diseases, obesity, and diabetes. Medications targeted to PPARs have been established to treat hyper-lipidemia (fibrates) and insulin resistance (glitazones). Thus, there is significant interest in developing new and specific ligands for these receptors. Here, we present the results of the screening of new ligands of PPAR alpha and PPAR gamma. Optical isomers of new chiral fibrates were synthesized and tested in cell-based assays. Compound (S)-7 showed a dual PPARU alpha/gamma activity, and its stereochemistry was crucial in receptor activation. Protease protection experiments suggested that this compound binds directly to PPAR. Moreover, computational studies showed that it properly docks to PPAR alpha and gamma ligand binding pockets. Interestingly, (S)-7 exhibited only a modest capacity to induce the differentiation of murine fibroblasts 3T3-L1 into adipocytes compared to rosiglitazone, a well-known PPAR gamma agonist.

  DOI：

  10.1021/jm0502844
• 作为产物：
  描述：

  在 盐酸 、 钾硼氢 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 13.5h， 生成 (2S)-2-Hydroxypentanoic acid methyl ester
  参考文献：
  名称：

  Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

  摘要：

  N-Acylation of prolinol with alpha-ketoacid chlorides results in concomitant hemiacetalization of the alpha-keto amide by the prolinol hydroxyl group, (R) or (S) alpha-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) alpha-alkyl mandelic acids with good stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00914-4

文献信息

• Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
  作者：Zechao Lin、Jiahong Li、Qingfei Huang、Qiuya Huang、Qiwei Wang、Lei Tang、Deying Gong、Jun Yang、Jin Zhu、Jingen Deng

  DOI：10.1021/acs.joc.5b00241

  日期：2015.5.1

  ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π

  设计并合成了一系列两亲性配体。具有配体的铑配合物被用于纯水中宽范围的长链脂族酮酸酯的不对称转移氢化。使用手性表面活性剂型催化剂2观察到α-，β-，γ-，δ-和ε-酮酸酯以及α-和β-酰氧基酮的定量转化率和出色的对映选择性（高达99％ee）。在金属硅油核中，催化剂与底物之间的长脂肪链之间的CH /π相互作用和长脂肪链的强疏水相互作用在催化过渡态中起着关键作用。胶束中金属催化位点与核心的疏水微环境之间的协同作用有助于实现高立体选择性。
• An evaluation of the substrate specificity and asymmetric synthesis potential of the cloned <scp>L</scp>-lactate dehydrogenase from <i>Bacillus</i><i>stearothermophilus</i>
  作者：Daniel Bur、Marcel A. Luyten、Hla Wynn、Louis R. Provencher、J. Bryan Jones、Marvin Gold、James D. Friesen、Anthony R. Clarke、J. John Holbrook

  DOI：10.1139/v89-161

  日期：1989.6.1

  assure its plentiful supply. Its specificity for keto acid substrates possessing straight- and branched-chain alkyl, cyclopropyl, or phenyl groups has been evaluated in preparative and kinetic terms, and compared with that of the mammalian pig heart enzyme (PHLDH). The specificities of BSLDH and PHLDH are similar, with branched alkyl-chain keto acids being poor substrates for both enzymes. Keywords: enzymes

  已经证明了嗜热脂肪芽孢杆菌 (BSLDH) 的 L-乳酸脱氢酶在立体特异性的、制备规模的将 α-酮酸还原为 (S)-α-羟基酸的潜在效用 > 99% ee。BSLDH 是一种稳定的嗜热酶，其基因已被克隆到高表达载体中以确保其充足供应。它对具有直链和支链烷基、环丙基或苯基的酮酸底物的特异性已在制备和动力学方面进行了评估，并与哺乳动物猪心脏酶 (PHLDH) 的特异性进行了比较。BSLDH 和 PHLDH 的特异性相似，支链烷基链酮酸是两种酶的不良底物。关键词：有机合成中的酶，乳酸脱氢酶，不对称合成。
• L-Lactate dehydrogenase: substrate specificity and use as a catalyst in the synthesis of homochiral 2-hydroxy acids
  作者：Mahn Joo. Kim、George M. Whitesides

  DOI：10.1021/ja00217a044

  日期：1988.4

  This note compares the substrate specificity of D-lactate dehydrogenase (D-LDH, EC 1.1.1.28) to that of L-lactate dehydrogenase (L-LDH, EC 1.1.1.27), illustrates three procedures that use D-LDH in synthesis and two methods for recycling NADH, and provides experimental details illustrating the use of D-LDH in organic synthesis.

  本说明比较了 D-乳酸脱氢酶 (D-LDH, EC 1.1.1.28) 与 L-乳酸脱氢酶 (L-LDH, EC 1.1.1.27) 的底物特异性，说明了在合成中使用 D-LDH 的三种程序和两种回收 NADH 的方法，并提供实验细节，说明 D-LDH 在有机合成中的用途。
• Total syntheses of pamamycin 607 and methyl nonactate: stereoselective cyclisation of homoallylic alcohols that had been prepared with remote stereocontrol using allylstannanes
  作者：Olivier Germay、Naresh Kumar、Christopher G. Moore、Eric J. Thomas

  DOI：10.1039/c2ob26801a

  日期：——

  then replaced by an N-(tert-butoxycarbonyl) group and O-debenzylation and oxidation gave the carboxylic acid 70 that corresponds to the C(1)–C(18) fragment of pamamycin 607 (1). Similar chemistry was used to prepare the C(1′)–C(11′) fragment 89 of the pamamycin, except that in this case the configuration of the secondary alcohol introduced by the allylstannane reaction had to be inverted using a Mitsunobu

  发现在路易斯酸存在下，使用苯基硒烯基氯或邻苯二甲酰亚胺，由氯化锡（IV）介导的（Z）-均烯丙基醇的环化反应，然后还原性去除苯基硒烯基，可得到具有优异立体控制的2,5-顺式-二取代四氢呋喃。 。使用该程序，通过锡（IV）立体选择性地制备了（2 S，4 S，8 R，6 Z）-9-苄氧基-2-叔丁基二苯基甲硅烷基氧基-8-甲基非-6-烯-4-醇（11））之间的氯化物促进反应（R）-5-苄氧基-4-甲基戊-2-烯基（三丁基）锡烷（3）和（S）-3-叔丁基二苯基甲硅烷基氧基丁醛（10），得到（2 S，3 R，6 S，8 S）-1脱硒后的-苄氧基-8-叔丁基二苯基甲硅烷氧基-3，6-环氧-2-甲基壬烷（13）。将该四氢呋喃选择性地脱保护，氧化和酯化，得到非乳酸甲酯（2）。已经建立了2，5-顺式-二取代的四氢呋喃的这种合成，将其用于完成帕马霉素607（1）的合成。（2 S，3 R从（R）立体选择性地制备，6S，8R）-1-苄氧基-8-
• A Highly Convergent Total Synthesis of (+)-Myxovirescine M2. Preliminary Communication
  作者：Dieter Seebach、Miguel A. Maestro、Michael Sefkow、Axel Neidlein、Francine Sternleld、Geo Adam、Thimo Sommerfeld

  DOI：10.1002/hlca.19910740846

  日期：1991.12.11

  (+)-D-ribonolactone, (S)-2-(hydroxymethyl)butanoate, and (2R,4S)-5-hydroxy-2,4-dimethylpenLanoate. Three new nucleophilic reagents, 8–10, for C-C bond formation have been used. The key steps of the synthesis are: a Suzuki coupling between an alkyl borane and a vinyl bromide (4 + 12e 13), a Julia olefinalion (14 + 17 18), and a Yamaguchi macrolactonizalion to form the 28-membered lactone (18 19), This

  抗生素myxovirescine中号2从7个积木（合成1 - 7，方案1），其中所采用的下列手性起始材料：（小号） -苹果酸，（+） - d-核糖酸内酯，（小号）-2- （羟甲基）丁酸酯和（2 R，4 S）-5-羟基-2,4-二甲基戊酸酯。三个新的亲核试剂，8 - 10，用于CC键形成已被使用。合成的关键步骤是：烷基硼烷与乙烯基溴（4 + 12e 13）之间的Suzuki偶联，朱莉娅（Julia） 烯醛（14 + 17 18）和山口大内酯化以形成28元内酯（18 19）。这种极其会聚的合成方法将允许制备31种已知的粘液新霉素分子。