(S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid | 225933-67-5

• 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: (S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid
• 英文别名: (2S)-4-Ethoxy-2-hydroxy-4-oxobutanoic Acid
• CAS: 225933-67-5
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: FFOKDOPEBQXHEH-BYPYZUCNSA-N

物化性质

• 沸点：
  358.6±27.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 以64%的产率得到ethyl (3S)-3,4-dihydroxy-3,4-O-isopropylidene-butanoate
  参考文献：
  名称：

  DIHYDROPYRIMIDO LOOP DERIVATIVE AS HBV INHIBITOR

  摘要：

  本发明公开了一种二氢嘧啶并环衍生物作为HBV抑制剂，特别涉及一种如下式（I）所示的化合物或其药用可接受的盐。

  公开号：

  US20170197986A1
• 作为产物：
  描述：

  L-苹果酸二乙酯 在 二甲基硫 、 硼烷 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.5h， 以60%的产率得到(S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid
  参考文献：
  名称：

  DIHYDROPYRIMIDO LOOP DERIVATIVE AS HBV INHIBITOR

  摘要：

  本发明公开了一种二氢嘧啶并环衍生物作为HBV抑制剂，特别涉及一种如下式（I）所示的化合物或其药用可接受的盐。

  公开号：

  US20170197986A1

文献信息

• METHODS AND COMPOSITIONS FOR PREVENTING OPIOID ABUSE
  申请人：Waterville Valley Technologies, Inc.

  公开号：US20160326182A1

  公开（公告）日：2016-11-10

  Abuse-resistant opioid compounds, drug delivery systems, pharmaceutical compositions comprising an opioid covalently bound to a chemical moiety are provided. Methods of delivering an active ingredient to a subject and methods of preventing opioid abuse are also provided.

  提供了耐滥用的阿片类化合物、药物输送系统、含有阿片类药物与化学基团共价结合的制药组合物。还提供了将活性成分输送给受试者的方法以及预防阿片类药物滥用的方法。
• A Unified Approach to Phytosiderophore Natural Products
  作者：Nicolas Kratena、Tobias Gökler、Lara Maltrovsky、Eva Oburger、Christian Stanetty

  DOI：10.1002/chem.202004004

  日期：2021.1.7

  the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative „east‐to‐west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l‐malic acid, threonines) were

  这项工作报告了 mugineic 酸和 avenic 酸家族（植物铁载体）的八种天然产物的简明全合成。三聚体产品的创新“从东到西”组装产生了高度的差异，使得最终产品的形成只需 10 或 11 个步骤，每个步骤所需的整体合成工作量最少。手性池起始材料（l-苹果酸、苏氨酸）用于外部构建单元，而中间构建单元通过非对映和对映选择性方法获得。这项工作的一个亮点在于直接制备差向异构羟基氮杂环丁烷氨基酸，它们本身就是有用的组成部分，从而能够首次合成 3''-羟基麦根酸和 3''-羟基-2'-脱氧麦根酸。
• Synthesis of [¹³C₄]-labeled 2′-deoxymugineic acid
  作者：Martin R. Walter、Daniel Artner、Christian Stanetty

  DOI：10.1002/jlcr.3242

  日期：2014.11

  The phytosiderophore 2′-deoxymugineic acid (DMA) is exuded via the root system by all grasses (including important crop plants like rice, wheat and barley) to mobilize Fe(III) from soil and improve plant Fe nutrition, crucial for high crop yields. Elucidation of the biogeochemistry of 2′-deoxymugineic acid in the rhizosphere requires its quantification in minute amounts. To this end, 13C4-DMA was synthesized for the first time, from cheap isotopically labeled starting materials. The synthetic route utilizes l-allyl(13C2)glycine and l-(2-13C)azetidine (13C)carboxylic acid as versatile labeled building blocks. The title compound was recently used as an internal standard for analysis of soil and plant samples allowing the first accurate quantification of DMA in these matrices by means of LC-MS/MS. It is furthermore used in tracer experiments investigating biodegradation of DMA in soil.

  所有禾本科植物（包括水稻、小麦和大麦等重要作物）都会通过根系渗出植物苷元 2′-脱氧木精酸 (DMA)，以动员土壤中的铁(III)，改善植物的铁营养状况，这对作物高产至关重要。要阐明根圈中 2′-脱氧木精酸的生物地球化学，需要对其进行微量定量。为此，我们首次利用廉价的同位素标记起始材料合成了 13C4-DMA。合成路线利用 l-烯丙基（13C2）甘氨酸和 l-（2-13C）氮杂环丁烷（13C）羧酸作为多功能标记构建模块。标题化合物最近被用作土壤和植物样品分析的内标，首次通过 LC-MS/MS 对这些基质中的 DMA 进行了精确定量。此外，它还被用于研究土壤中 DMA 生物降解的示踪实验。
• Plant growth regulators and Axl and immune checkpoint inhibitors from the edible mushroom <i>Leucopaxillus giganteus</i>
  作者：Irine Yunhafita Malya、Jing Wu、Etsuko Harada、Masaaki Toda、Corina N D’Alessandro-Gabazza、Taro Yasuma、Esteban C Gabazza、Jae-Hoon Choi、Hirofumi Hirai、Hirokazu Kawagishi

  DOI：10.1080/09168451.2020.1743170

  日期：2020.7.2

  A novel compound, (R)-4-ethoxy-2-hydroxy-4-oxobutanoic acid (1), and six known compounds (2–7) were isolated from the fruiting bodies of the wild edible mushroom Leucopaxillus giganteus. The planar structure of 1 was determined by the interpretation of spectroscopic data analysis. The absolute configuration of 1 was determined by comparing specific rotation of the synthetic compounds. In the plant regulatory assay, the isolated compounds (1–7) and the chemically prepared compounds (8–10) were evaluated their biological activity against the lettuce (Lactuca sativa) growth. Compounds 1 and 3–10 showed the significant regulatory activity of lettuce growth. 1 showed the strongest inhibition activity among the all the compounds tested. In the lung cancer assay, all the compounds were assessed the mRNA expression of Axl and immune checkpoints (PD-L1, PD-L2) in the human A549 alveolar epithelial cell line by RT-PCR. Compounds 1–10 showed significant inhibition activity against Axl and/or immune checkpoint.

  摘要：从野生可食用蘑菇Leucopaxillus giganteus的子实体中分离出一种新化合物(R)-4-乙氧基-2-羟基-4-酮丁酸（1）和六种已知化合物（2-7）。化合物1的平面结构通过解释光谱数据分析确定。通过比较合成化合物的比旋光确定了化合物1的绝对构型。在植物调节作用实验中，评估了分离的化合物（1-7）和化学制备的化合物（8-10）对莴苣（Lactuca sativa）生长的生物活性。化合物1和3-10表现出显著的调节莴苣生长的活性。在肺癌实验中，通过RT-PCR评估了所有化合物对人类A549肺泡上皮细胞系中Axl和免疫检查点（PD-L1，PD-L2）的mRNA表达。化合物1-10表现出对Axl和/或免疫检查点的显著抑制活性。
• A Facile Synthesis of (S)-4-Hydroxypyrrolidin-2-one from (S)-Malic Acid
  作者：Masahiko Seki、Kazuhiko Kondo

  DOI：10.1055/s-1999-3460

  日期：1999.5

  The chiral diol methyl 3,4-dihydroxybutanoate 4b obtained from (S)-malic acid dimethyl ester (3b) was subjected to regioselective tosylation to give the tosylate 6 in good yield. Subsequent treatment of 6 with aqueous ammonia afforded (S)-4-hydroxypyrrolidin-2-one (1) through three steps in 32% overall yield from 3b.

  对从 (S)- 苹果酸二甲酯 (3b) 中得到的手性二醇 3,4- 二羟基丁酸甲酯 4b 进行区域选择性对甲苯磺酰化，得到对甲苯磺酰化物 6，收率很高。随后用氨水处理 6，通过三个步骤从 3b 得到 (S)-4-羟基吡咯烷-2-酮 (1)，总收率为 32%。