2-氨基-3-羟基-(2S,3R)丁酰胺单盐酸盐 | 33209-01-7

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-氨基-3-羟基-(2S,3R)丁酰胺单盐酸盐
• 中文别名: 苏氨酸酰胺盐酸盐
• 英文名称: (2S,3R)-2-amino-3-hydroxybutanamide hydrochloride
• 英文别名: [(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]azanium;chloride
• CAS: 33209-01-7
• 化学式: C₄H₁₀N₂O₂*ClH
• mdl: MFCD00058288
• 分子量: 154.597
• InChiKey: LZQCOMULTLYITH-MUWMCQJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.02
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  89.3
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Thr-NH2 HCl
Synonyms: L-Threonine amide hydrochloride

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: H-Thr-NH2 HCl
CAS number: 33209-01-7

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C4H10N2O2.ClH
Molecular weight: 154.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氨基-3-羟基-(2S,3R)丁酰胺单盐酸盐 、 4-硝基苯基乙酸酯 生成 N-acetyl-L-threoninamide
  参考文献：
  名称：

  Fauchere, Jean-Luc; Pliska, Vladimir, European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 369 - 376

  摘要：

  DOI：
• 作为产物：
  描述：

  L-苏氨酸盐酸盐 在 hexamethylphosphorous triamide dichloride 、 氨 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到2-氨基-3-羟基-(2S,3R)丁酰胺单盐酸盐
  参考文献：
  名称：

  Appel, Rolf; Hiester, Ernst, Chemische Berichte, 1983, vol. 116, # 5, p. 2037 - 2040

  摘要：

  DOI：

文献信息

• In vitro synthesis of mucin-type O-glycans using saccharide primers comprising GalNAc-Ser and GalNAc-Thr residues
  作者：Ryuma Sakura、Kaori Nagai、Yuka Yagi、Yoshihisa Takahashi、Yoshimi Ide、Yuki Yagi、Daiki Yamamoto、Mamoru Mizuno、Toshinori Sato

  DOI：10.1016/j.carres.2021.108495

  日期：2022.1

  synthesized as saccharide primers to prime mucin-type O-glycan biosynthesis in cells. Upon incubating human gastric cancer MKN45 cells with the saccharide primers, 22 glycosylated products were obtained, and their structures were analyzed using liquid chromatography-mass spectrometry and enzyme digestion. The amounts of glycosylated products were dependent on the amino acid residues in the saccharide primers

  已知蛋白质中丝氨酸或苏氨酸残基的粘蛋白型O-糖基化是主要的翻译后修饰之一。在这项研究中，两种新型烷基糖苷，N α -lauryl - O -(2-acetamido-2-deoxy-α- d -galactopyranosyl ) -l -serineamide (GalNAc-Ser-C12) 和N α -lauryl - O- (2-acetamido-2-deoxy-α- d -galactopyranosyl ) -l -threonineamide (GalNAc-Thr-C12) 作为糖类引物合成O型粘蛋白-细胞中的聚糖生物合成。用糖类引物孵育人胃癌 MKN45 细胞后，获得了 22 种糖基化产物，并使用液相色谱-质谱法和酶消化法分析了它们的结构。糖基化产物的量取决于糖类引物中的氨基酸残基。例如，体外T 抗原 (Galβ1-3GalNAc)、岩藻糖基-T (Fucα1-2Galβ1-3GalNAc)
• PROCESS AND INTERMEDIATES FOR SYNTHESIS OF PEPTIDE COMPOUNDS
  申请人：Naurex, Inc

  公开号：US20190031715A1

  公开（公告）日：2019-01-31

  Disclosed is a new process and intermediates for preparing dipyrrolidine peptide compounds such as, for example, rapastinel. Advantageously, the process may be industrially scalable and cost-effective and use less toxic reagents and/or solvents. Further, the process may be used to prepare peptide compounds having improved purity.

  披露了一种用于制备双吡咯啉肽类化合物（例如rapastinel）的新工艺和中间体。该工艺具有工业可扩展性和经济性，并使用较少毒性试剂和/或溶剂。此外，该工艺可用于制备纯度更高的肽类化合物。
• TRPV3 Modulators
  申请人：Clapham Bruce

  公开号：US20120245124A1

  公开（公告）日：2012-09-27

  Disclosed herein are modulators of TRPV3 of formula (I) wherein X 1 , X 2 , R 1 , R 2 , R x , and n are as defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also presented.

  本文披露了具有如下式（I）的TRPV3调节剂，其中X1、X2、R1、R2、Rx和n如规范中定义。还提供了包含这种化合物的组合物以及使用这种化合物和组合物治疗疾病和疾病的方法。
• Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C─N coupling reaction of aryl halides and α-aminoamides
  作者：Xiangting Min、Xiaoyu Li、Yu Wang、Yawen Dong、Jingjing Tang、Jing Wang、Jianhui Liu

  DOI：10.1016/j.tet.2018.03.003

  日期：2018.5

  A DMEDA-promoted and copper-catalyzed approach has been designed for the coupling of aryl halides and chiral α-aminoamides to afford a range of functionalized chiral α-amino anilides. This method has a higher yield and better reproducibility than those under ligand-free conditions. Of the two amino groups in the same molecule, only the amide NH2 is observed to react, showing high regioselectivity.

  已经设计了一种DMEDA促进的铜催化方法，用于芳基卤化物和手性α-氨基酰胺的偶联，以提供一系列官能化的手性α-氨基苯胺。与在无配体条件下相比，该方法具有更高的收率和更好的重现性。在同一分子中的两个氨基中，仅酰胺NH 2被观察到反应，显示出高区域选择性。此外，不会发生消旋化，并且ee可以达到99％。对于某些含羟基的底物，例如1-酪氨酸酰胺和1-苏氨酸酰胺，需要添加相转移催化剂（15-Crown-5）来进行这种转化。
• Scale-Up Synthesis and Identification of GLYX-13, a NMDAR Glycine-Site Partial Agonist for the Treatment of Major Depressive Disorder
  作者：Wenchao Li、Jingjian Liu、Minghua Fan、Zhongtang Li、Yin Chen、Guisen Zhang、Zhuo Huang、Liangren Zhang

  DOI：10.3390/molecules23050996

  日期：——

  GLYX-13, a NMDAR glycine-site partial agonist, was discovered as a promising antidepressant with rapidly acting effects but no ketamine-like side effects. However, the reported synthetic process route had deficiencies of low yield and the use of unfriendly reagents. Here, we report a scaled-up synthesis of GLYX-13 with an overall yield of 30% on the hectogram scale with a column chromatography-free strategy, where the coupling and deprotection reaction conditions were systematically optimized. Meanwhile, the absolute configuration of precursor compound of GLYX-13 was identified by X-ray single crystal diffraction. Finally, the activity of GLYX-13 was verified in the cortical neurons of mice through whole-cell voltage-clamp technique.

  GLYX-13是一种NMDAR甘氨酸位点的部分激动剂，被发现是一种具有迅速作用效果且没有类氟氯噪啡副作用的有前景的抗抑郁药。然而，已有的合成路线存在产率低和使用不友好的试剂的缺陷。在这里，我们报告了一种GLYX-13的放大合成方法，在百克规模上总体产率为30%，并采用了无柱色谱策略，系统优化了耦合和去保护反应条件。同时，通过X射线单晶衍射鉴定了GLYX-13前体化合物的绝对构型。最后，GLYX-13的活性通过全细胞电压钳技术在小鼠皮层神经元中得到了验证。