(2R,3S)-(1-氨基甲酰基-2-羟基丙基)氨基甲酸苄酯 | 49705-98-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - Cbz-氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2R,3S)-(1-氨基甲酰基-2-羟基丙基)氨基甲酸苄酯
• 中文别名: CBZ-L-苏氨酰胺；Cbz-苏氨酰胺；N-苄氧羰基-L-苏胺酰胺；Z-L-苏氨酰胺
• 英文名称: N-benzyloxycarbonyl-L-threonine amide
• 英文别名: benzyl N-[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]carbamate
• CAS: 49705-98-8
• 化学式: C₁₂H₁₆N₂O₄
• mdl: MFCD00038587
• 分子量: 252.27
• InChiKey: PYZXYZOBPGPOFQ-SCZZXKLOSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  508.4±50.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（少量溶解）、DMSO（少量溶解）、乙酸乙酯（少量溶解）、甲醇（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Z-Thr-NH2
CAS-No. : 49705-98-8
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Z-L-threoninamide
Formula : C12H16N2O4
Molecular Weight : 252,27 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 89 - 91 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(1-氨基甲酰基-2-羟基丙基)氨基甲酸苄酯 在 钯 氢气 作用下， 以 甲醇 为溶剂， 生成 [R-(R*,S*)]-2-氨基-3-羟基丁酰胺
  参考文献：
  名称：

  Seitenkettenwechselwirkung in serin- oder threoninhaltigen Asparagylpeptiden

  摘要：

  DOI：

  10.1515/bchm2.1963.332.1.38
• 作为产物：
  描述：

  N-苄氧羰基-L-苏氨酸 在 氨 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 (2R,3S)-(1-氨基甲酰基-2-羟基丙基)氨基甲酸苄酯
  参考文献：
  名称：

  大环抗生素微球菌素 P 的全合成

  摘要：

  实现了大环抗生素微球菌素 P1 (1) 的首次全合成。这种抗生素具有独特的结构，由称为片段 A、B、C 和 D 的四种成分构成。特别是，1 的中央吡啶骨架（片段 A）和环外侧链（片段 D）的结构是与类似抗生素微球菌素 P (2) 的抗生素略有不同。通过对合成方法2的各种化学修饰，从乙基2-[6-二甲氧基甲基-2-(1-)合成中心2,3,6-三(取代噻唑基)吡啶链段[片段A-C]15乙氧基乙烯基)-3-吡啶基]噻唑-4-羧酸酯 (9)，然后将 15 与独立合成的片段 B 和 D 部分偶联，得到受保护的片段 ABCD。

  DOI：

  10.1246/bcsj.72.1561

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)
• [EN] SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS SPIROLACTAMES D'UN RÉCEPTEUR NMDA ET LEURS UTILISATIONS
  申请人：NAUREX INC

  公开号：WO2014120800A1

  公开（公告）日：2014-08-07

  Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

  揭示了在调节NMDA受体活性方面具有增强效力的化合物。这些化合物可用于治疗抑郁症和相关疾病。此外，还披露了口服制剂和其他药学上可接受的化合物给药形式，包括静脉注射制剂。
• 1-[苄氧羰基-氨基]-2-甲基-4-氧代-3-叔丁磺酰基-3-氨杂环丁烷的合成
  申请人：山东金城柯瑞化学有限公司

  公开号：CN109232349A

  公开（公告）日：2019-01-18

  本发明属于医药合成技术领域，具体的涉及一种1‑[苄氧羰基‑氨基]‑2‑甲基‑4‑氧代‑3‑叔丁磺酰基‑3‑氨杂环丁烷的合成。向反应釜中加入N‑苄氧羰基‑L‑苏氨酸酰胺固体，加入有机溶剂搅拌降温，然后加入甲基磺酰氯和缚酸剂得到混合反应液；加入三氧化硫‑有机碱络合物，升温反应，升温过程蒸出溶剂，反应完毕，蒸干溶剂后得到N‑磺基‑N‑苄氧簇基‑0‑甲烷磺酸基‑L‑苏氨酸酰胺钠盐；加水溶解，将水溶液加入到热的氢氧化钠溶液中，降温抽滤得到1‑[苄氧羰基‑氨基]‑2‑甲基‑4‑氧代‑3‑叔丁磺酰基‑3‑氨杂环丁烷，加氢验证2h之内反应完毕。该方法反应时间短，绿色环保，工艺简单，成本较低，总收率高。
• 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。
• Acceptor-Controlled Transfer Dehydration of Amides to Nitriles
  作者：Hiroyuki Okabe、Asuka Naraoka、Takahiro Isogawa、Shunsuke Oishi、Hiroshi Naka

  DOI：10.1021/acs.orglett.9b01657

  日期：2019.6.21

  dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired

  通过使用二氯乙腈作为水受体，在温和的水性条件下钯催化的伯酰胺脱水有效地进行为腈。设计该转移脱水催化的关键是确定一种有效的水受体二氯乙腈，该水受体在Pd催化剂的帮助下优先于酰胺而不是其他极性官能团反应，并使所需的反应体系趋于能动，从而驱动脱水。