二乙基 (2S,3S)-(+)-2,3-环氧琥珀酸 | 73890-18-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 二乙基 (2S,3S)-(+)-2,3-环氧琥珀酸
• 中文别名: 二乙基(28,3S)-(+)-2,3-环氧琥珀酸酯；二乙基(2S,3S)-(+)-2,3-环氧琥珀酸
• 英文名称: (2S,3S)-diethyl oxirane-2,3-dicarboxylate
• 英文别名: diethyl (+)-(2S,3S)-2,3-epoxysuccinate；diethyl (2S,3S)-oxirane-2,3-dicarboxylate；diethyl (2S,3S)-(+)-threo-2,3-epoxysuccinate
• CAS: 73890-18-3
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: LDFQMMUIJQDSAB-WDSKDSINSA-N

物化性质

• 沸点：
  233.7±30.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（少量溶解）、乙醇（少量溶解）、乙酸乙酯（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S37/39

SDS

Name:	Diethyl (2S 3S)-(+)-2 3-epoxysuccinate 98% Material Safety Data Sheet
Synonym:
CAS:	73890-18-3

Section 1 - Chemical Product MSDS Name:Diethyl (2S 3S)-(+)-2 3-epoxysuccinate 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
73890-18-3	Diethyl (2S,3S)-(+)-2,3-epoxysuccinate	98%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 73890-18-3: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula:
Molecular Weight: 188.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 73890-18-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diethyl (2S,3S)-(+)-2,3-epoxysuccinate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 73890-18-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 73890-18-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 73890-18-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二乙基 (2S,3S)-(+)-2,3-环氧琥珀酸 在 N-甲基吗啉 、 氢氧化钾 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 阿洛司他丁
  参考文献：
  名称：

  环氧琥珀酰抑制剂使木瓜蛋白酶失活的机理研究。

  摘要：

  合成了环氧琥珀酰肽半胱氨酸蛋白酶抑制剂的类似物EP-475（2a），其中的游离羧酸盐已被异羟肟酸，酰胺，甲基酮，羟基和乙酯官能团取代。确定这些抑制剂对木瓜蛋白酶的抑制率。结果表明，含羰基的官能团对于良好的活性是必需的。确定了不可电离的EP-475（2a）类似物对木瓜蛋白酶抑制作用的pH依赖性。发现抑制作用取决于木瓜蛋白酶的两个酸性离子化（pKas分别为3.93和4.09）。讨论了环氧琥珀酰肽与木瓜蛋白酶的作用机理。

  DOI：

  10.1021/jm950445b
• 作为产物：
  描述：

  L-苹果酸二乙酯 在 碘 、 lithium diisopropyl amide 作用下， 生成 二乙基 (2S,3S)-(+)-2,3-环氧琥珀酸
  参考文献：
  名称：

  Herstellung冯赤-2-Hydroxybernsteinsäure-Derivaten AUSÄpfelsäureester。福尔蒂米特·米特隆

  摘要：

  苹果酸酯制备赤型-2-羟基琥珀酸衍生物

  DOI：

  10.1002/hlca.19800630118

文献信息

• Two-Step Labeling of Endogenous Enzymatic Activities by Diels-Alder Ligation
  作者：Lianne I. Willems、Martijn Verdoes、Bogdan I. Florea、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1002/cbic.201000280

  日期：——

  Double labeling: A Diels–Alder‐based ligation strategy for activity‐based profiling of endogenously expressed proteases by using a panel of diene‐derivatized probes and a dienophile‐functionalized fluorescent tag has been developed. This procedure is fully orthogonal with respect to the Staudinger–Bertozzi ligation, thus allowing both methods to be used in the same sample to independently label two different

  双重标记：已开发出一种基于Diels-Alder的连接策略，可通过使用一组二烯衍生化的探针和亲二烯体官能化的荧光标签对内源表达的蛋白酶进行基于活性的谱分析。此程序相对于Staudinger-Bertozzi连接完全正交，因此允许在同一样品中使用两种方法来独立标记两种不同的酶活性。
• Konfiguration und enantioselektive Synthese des Pilzmetaboliten WF14861
  作者：Richard Detterbeck、Manfred Hesse

  DOI：10.1002/hlca.200390015

  日期：2003.1

  A short enantioselective synthesis of the cathepsine inhibitor WF14861 (1) from the funghi Colletotrichum sp. as well as of its diasteroisomer 21 is presented. Comparison of the NMR data of the final products and, in particular, of the [α]D values of the intermediates allowed the confirmation of the formerly proposed structure 1. In addition, the so far unknown absolute configuration of all three stereogenic

  从Funghi Colletotrichum sp。短时对映体合成组织蛋白酶抑制剂WF14861（1）。以及它的非对映异构体21。通过比较最终产物的NMR数据，尤其是中间体的[ α ] D值，可以确认先前提出的结构1。另外，通过该合成可以建立迄今未知的WF14861的所有三个立体异构中心的绝对构型。
• Design, Synthesis, and Structure–Activity Relationship Study of Epoxysuccinyl–Peptide Derivatives as Cathepsin B Inhibitors
  作者：Xiaoye Zhang、Xiaohong Yang、Hongqiang Wang、Song Li、Kun Guo、Dan Jiang、Junhai Xiao、Di Liang

  DOI：10.1248/bpb.b17-00075

  日期：——

  Cathepsin B is a lysosomal cysteine protease involved in many diseases. The present research demonstrates that derivatives of epoxysuccinyl–peptide are effective and selective cathepsin B inhibitors. We synthesized a series of epoxysuccinyl–peptide derivatives based on the well-known cathepsin B inhibitor E64d. Specifically, we substituted the 2-methylpropane group at the R1 position of E64d with a sulfane, such as ethyl(methyl) sulfane or benzyl(methyl) sulfane. We also designed and synthesized a library of molecules with various substituents at the R2 position of E64d to replace 2-methylbutane. By studying the structure–activity relationships of these newly synthesized molecules as cathepsin B inhibitors, we demonstrated that substituting ethyl(methyl) sulfane for 2-methylbutane (R2) of E64d improves the inhibitory activity and selectivity for cathepsin B inhibition. Our new cathepsin B inhibitors were highly effective and selective.

  组织蛋白酶B是一种溶酶体半胱氨酸蛋白酶，参与多种疾病过程。目前的研究表明，环氧琥珀酰肽衍生物是有效的且选择性的组织蛋白酶B抑制剂。我们基于已知的组织蛋白酶B抑制剂E64d合成了一系列环氧琥珀酰肽衍生物。具体来说，我们将E64d的R1位上的2-甲基丙烷基团替换为硫烷，如乙基(甲基)硫烷或苄基(甲基)硫烷。我们还设计并合成了一系列分子，其中E64d的R2位上的2-甲基丁烷被各种取代基替代。通过对这些新合成的分子作为组织蛋白酶B抑制剂的构效关系研究，我们证明了用乙基(甲基)硫烷替代E64d的2-甲基丁烷（R2）可以提高抑制活性并增强对组织蛋白酶B抑制的选择性。我们的新型组织蛋白酶B抑制剂表现出高度的有效性和选择性。
• 2, 3-Butanediamide Epoxide Compound and Preparation Method and Use Thereof
  申请人：INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY ACADEMY OF MILITARY MEDICAL SCIENCES P.L.A. CHINA

  公开号：US20160115160A1

  公开（公告）日：2016-04-28

  Provided are a compound of formula I which can be used as a drug against small RNA virus infections, and optical isomers, pharmaceutically acceptable salts, solvates or hydrates thereof. Also provided are the preparation method of the compound, the method for using the compound for treating bacterial infections and the use of the compound in the preparation of a drug for preventing and/or treating viral diseases caused by small RNA viruses.

  提供了一种可以用作抗小RNA病毒感染药物的I式化合物，以及其光学异构体、药学上可接受的盐、溶剂合物或水合物。还提供了该化合物的制备方法，用于治疗细菌感染的方法以及用于制备预防和/或治疗由小RNA病毒引起的病毒性疾病药物的方法。
• Process for the production of pentostatin aglycone and pentostatin
  申请人：——

  公开号：US20040181052A1

  公开（公告）日：2004-09-16

  A novel, scaleable and improved process for preparing pentostatin and its analogs is disclosed. The method comprises the diastereospecific synthesis of the nucleobase from commercially available L-Dialkyl tartarates.

  揭示了一种用于制备戊糖核苷和其类似物的新型、可扩展和改进的工艺。该方法包括从市售的L-二烷基酒石酸盐合成核碱的对映体特异性合成。