methyl 3,4-dihydroxybutanoate | 88246-12-2

• 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: methyl 3,4-dihydroxybutanoate
• 英文别名: 3,4-dihydroxybutyric acid-1-methyl ester；3,4-dihydroxy methyl butyrate ester；methyl-3,4-dihydroxybutyrate
• CAS: 88246-12-2
• 化学式: C₅H₁₀O₄
• mdl: MFCD09996821
• 分子量: 134.132
• InChiKey: KCKWOJWPEXHLOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  methyl 3,4-dihydroxybutanoate 在 对甲苯磺酸 作用下， 生成 (±)-3-羟基-r-丁内酯
  参考文献：
  名称：

  单羟基和二羟基呋喃糖，吡喃糖和乙二糖的合成，用于制备天然产物类似物文库

  摘要：

  许多具有生物活性的天然产物都含有呋喃糖酶和带有单羟基和二羟基取代基的吡喃糖酶。但是，对此类分子的许多结构活性研究都是在糖苷配基上进行的，而没有关注相应的碳水化合物成分。因此，几乎没有能够快速制备单和二羟基呋喃糖酶和单和二羟基吡喃糖的合成方法，也没有关于3，4-二羟基氧戊糖的报道。在本文中，我们报告了正交保护的五元，六元和七元碳水化合物衍生物的实用合成。合成这些分子的简洁方式允许快速制备类似物，旨在发现吡喃糖骨架上的环大小和单个羟基部分的作用。

  DOI：

  10.1021/jo050558v
• 作为产物：
  描述：

  3-丁烯酸甲酯 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 生成 methyl 3,4-dihydroxybutanoate
  参考文献：
  名称：

  Exploitation of a Novel Binding Pocket in Human Lipoprotein-Associated Phospholipase A2 (Lp-PLA₂) Discovered through X-ray Fragment Screening

  摘要：

  Elevated levels of human lipoprotein-associated phospholipase A2 (Lp-PLA(2)) are associated with cardiovascular disease and dementia. A fragment screen was conducted against Lp-PLA(2) in order to identify novel inhibitors. Multiple fragment hits were observed in different regions of the active site, including some hits that bound in a pocket created by movement of a protein side chain (approximately 13 A from the catalytic residue Ser273). Using structure guided design, we optimized a fragment that bound in this pocket to generate a novel low nanomolar chemotype, which did not interact with the catalytic residues.

  DOI：

  10.1021/acs.jmedchem.6b00212

文献信息

• Shifting the equilibrium of a biocatalytic cascade synthesis to enantiopure epoxides using anion exchangers
  作者：Joerg H. Schrittwieser、Iván Lavandera、Birgit Seisser、Barbara Mautner、Jeffrey H. Lutje Spelberg、Wolfgang Kroutil

  DOI：10.1016/j.tetasy.2009.02.035

  日期：2009.3

  successfully employed to shift the equilibrium of a one-pot, two-step, two-enzyme cascade reaction affording enantiopure epoxides starting from prochiral α-chloroketones. The α-chloroketones were asymmetrically reduced employing an alcohol dehydrogenase and then transformed further to the corresponding epoxides employing halohydrin dehalogenases. Each epoxide enantiomer could be obtained with up to 93% conversion

  负载氢氧化物的阴离子交换剂已成功用于改变一锅，两步，两酶级联反应的平衡，从而提供从前手性α-氯酮开始的对映体纯环氧化合物。用醇脱氢酶不对称还原α-氯酮，然后用卤代醇脱卤酶将其进一步转化为相应的环氧化物。可以以对映体纯的形式（＞ 99％ee）以高达93％的转化率获得每种环氧对映体。与以前的研究相反，由于α-氯酮还原过程中有利于卤代醇的形成，因此可以减少氢化物供体（2-丙醇）的量。
• A heterogenized cobaltate catalyst on a bis-imidazolium-based covalent triazine framework for hydroesterification of epoxides
  作者：Senkuttuvan Rajendiran、Gunniya Hariyanandam Gunasekar、Sungho Yoon

  DOI：10.1039/c8nj02292e

  日期：——

  heterogeneous catalyst exhibits advantages over its homogeneous counterpart in the synthesis of β-hydroxyesters from epoxides. However, leaching of cobaltate from the catalytic support decreases the selectivity and recyclability of the catalyst. To overcome such drawbacks, a bis-imidazolium-based covalent triazine framework (CTF) is employed as a catalytic support for the hydroesterification catalyst to reduce

  基于咪唑鎓钴酸盐的非均相催化剂在由环氧化物合成β-羟基酯方面显示出优于其均相对应物的优点。但是，从催化载体中浸出钴酸盐会降低催化剂的选择性和可回收性。为了克服这些缺点，使用了基于双咪唑基的共价三嗪骨架（CTF）作为加氢酯化催化剂的催化载体，以通过多咪唑基团的分子内阴离子稳定作用来减少钴的浸出，从而获得了优异的选择性。 β-羟基酯具有前所未有的可回收性。
• 5-Hydroxy[1,2]oxazinan-3-ones as potential carbapenem and D-ala-D-ala surrogates
  作者：Saul Wolfe、Christiana Akuche、Stephen Ro、Marie-Claire Wilson、Chan-Kyung Kim、Zheng Shi

  DOI：10.1139/v03-123

  日期：2003.8.1

  proposed new family of antibacterial agents targeted to the penicillin receptor. The glycine and alanine members of the family have been synthesized, as racemates, in seven steps from the four-carbon synthon diketene and the tert-butyl esters of N-hydroxyglycine and N-hydroxyalanine. Numerous alternatives to diketene have also been examined, but these lead mainly to five-membered cyclic hydroxamates

  标题化合物是氨基酸，其氮原子被包含在带有 C5-羟基的六元环状异羟肟酸酯中。它们属于一个提议的针对青霉素受体的新型抗菌剂家族。该家族的甘氨酸和丙氨酸成员作为外消旋物，从四碳合成子双烯酮和 N-羟基甘氨酸和 N-羟基丙氨酸的叔丁酯分七个步骤合成。还研究了许多双烯酮的替代品，但这些主要导致五元环异羟肟酸酯。导致此综合程序的理论考虑进行了一些详细的讨论。它们包括分析天然和非天然青霉素替代物的结构，分析青霉素药效团，青霉素阻断细菌细胞壁合成的化学反应。甘氨酸衍生物相对于藤黄微球菌表现出微弱但真实的活性。丙氨酸衍生物，更接近于...
• N,N′-Di-Boc-Substituted Thiourea as a Novel and Mild Thioacylating Agent Applicable for the Synthesis of Thiocarbonyl Compounds
  作者：Biao-Lin Yin、Zhao-Gui Liu、Jian-Cun Zhang、Zheng-Rong Li

  DOI：10.1055/s-0029-1219273

  日期：2010.3

  Stable and readily available N,N′-di-Boc-substituted thiourea, when activated with trifluoroacetic acid anhydride, was used as a novel thioacylating agent. Through the thioacylation of nucleophiles, such as amines, alcohols, thiols, sodium benzene­thiolate, and sodium malonates with N,N′-di-Boc-substituted thiourea, a series of thiocarbonyl compounds were prepared under mild conditions with good chemical selectivity and functional group tolerance.

  稳定且易于获得的N,N′-双-Boc取代硫脲，在三氟乙酸酐活化下，被用作一种新型硫代酰化剂。通过对亲核试剂如胺、醇、硫醇、苯硫醇钠和丙二酸钠与N,N′-双-Boc取代硫脲的硫代酰化反应，一系列硫代羰基化合物在温和条件下以良好的化学选择性和官能团耐受性被制备出来。
• [EN] NOVEL BORONATE ESTERS<br/>[FR] NOUVEAUX ESTERS DE BORONATE
  申请人：BIOCON LTD

  公开号：WO2004113314A1

  公开（公告）日：2004-12-29

  The present invention relates to optically active dihydroxy hexanoate derivatives, boronate esters of formula (IIa) which are useful intermediates for the synthesis of HMG-CoA enzyme inhibitors like atorvastatin, cerivastatin, rosuvastatin, pitavastatin, fluvastatin. Ar = unsubstituted or substituted aryl or heteroaryl, R3 = alkyl from 1 to 8 carbons, aryl or aralkyl, R4 = O, OH, CN or a halogen and a = single bond or a double bond.

  本发明涉及光学活性的二羟基己酸酯衍生物，具有公式（IIa）的硼酸酯，这些化合物是用于合成类似阿托伐他汀、西利伐他汀、罗伐他汀、匹伐他汀、氟伐他汀等HMG-CoA酶抑制剂的中间体。其中Ar = 未取代或取代的芳基或杂环芳基，R3 = 1至8个碳的烷基，芳基或芳基烷基，R4 = O、OH、CN或卤素，a = 单键或双键。

表征谱图