N-CBZ-O-苄基苏氨酸 | 69863-36-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苏氨酸类衍生物
• 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: N-CBZ-O-苄基苏氨酸
• 中文别名: N-Cbz-O-苄基苏氨酸；Z-O-苄基苏氨酸；(3R,2S)-3-苄氧基-2-苄氧基羰基氨基丁酸
• 英文名称: N-(Cbz)-O-(benzyl) ether L-threonine
• 英文别名: Z-Thr(Bzl)-OH；(2S,3R)-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 69863-36-1
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: FVKJXAYBJIAXAU-PBHICJAKSA-N

物化性质

• 熔点：
  77-80 °C(lit.)
• 沸点：
  539.3±50.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Thr(bzl)-oh
Synonyms:

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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: Z-Thr(bzl)-oh
CAS number: 69863-36-1

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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: C19H21NO5
Molecular weight: 343.4

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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.

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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：

  N-CBZ-O-苄基苏氨酸 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到O-(苯基甲基)-L-苏氨酸
  参考文献：
  名称：

  使用催化剂毒物的新型氢化作用：通过添加含氮碱，化学选择性抑制O-苄基保护基的氢解反应

  摘要：

  通过向Pd / C催化的氢化系统中添加适当的含氮碱，可以实现温和的，选择性的，不同于脂肪族和芳香族苄基醚的各种可还原官能团的化学选择氢化方法。

  DOI：

  10.1016/s0040-4020(98)00882-5
• 作为产物：
  描述：

  (2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate oxalate 、 氯甲酸苄酯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 1.0h， 以88%的产率得到N-CBZ-O-苄基苏氨酸
  参考文献：
  名称：

  Solution-Phase Peptide Synthesis; Synthesis of 'North-Western' and 'South-Eastern' Fragments of the Antifungal Cyclodepsipeptide Petriellin A

  摘要：

  本报告介绍了两种高度修饰的肽的溶液相合成过程，一种是六聚体，另一种是七聚体，它们构成了抗真菌环脱肽 Petriellin A 的两半。

  DOI：

  10.1071/ch08132

文献信息

• A rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for 10b-hydroxy-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones
  作者：Steven V. Ley、Ed Cleator、Peter R. Hewitt

  DOI：10.1039/b308288a

  日期：——

  A two-step selenocyclisation–oxidative deselenation sequence was used to establish the 3a-hydroxy-pyrrolo[2,3-b]indole core; these tricycles were used as effective precursors to 10b-hydroxy-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones.

  采用两步硒杂环化-氧化脱硒序列构建了3a-羟基吡咯并[2,3-b]吲哚核心；这些三环化合物被用作高效前体，转化为10b-羟基吡嗪并[1′,2′:1,5]吡咯并[2,3-b]吲哚-1,4-二酮。
• Selective inhibition of benzyl ether hydrogenolysis with Pd/C due to the presence of ammonia, pyridine or ammonium acetate
  作者：Hironao Sajiki

  DOI：10.1016/0040-4039(95)00527-j

  日期：1995.5

  Ammonia, pyridine and ammonium acetate were found to be extremely effective as inhibitors of Pd/C catalyzed benzyl ether hydrogenolysis. While olefin, Cbz, benzyl ester and azide functionalities were hydrogenated smoothly, benzyl ethers were not cleaved in the presence of these additives.

  发现氨，吡啶和乙酸铵作为Pd / C催化的苄基醚氢解的抑制剂极为有效。尽管烯烃，Cbz，苄基酯和叠氮化物官能团被顺利氢化，但在这些添加剂的存在下苄基醚​​没有被裂解。
• Solid Phase Synthesis of Hydroxamic Acids
  作者：Sharon M. Dankwardt

  DOI：10.1055/s-1998-1774

  日期：1998.7

  The solid phase synthesis of hydroxamic acids is presented. Carboxylic acid ester linked, polymer-supported CBZ-protected amino acids were displaced from the resin with aqueous hydroxylamine to provide the corresponding hydroxamic acids.

  羟肟酸的固相合成方法如下。首先，将带有酯键的聚合物支持的CBZ保护氨基酸从树脂上释放下来，然后用水合羟胺处理，生成相应的羟肟酸。
• Rapid Combinatorial Synthesis of Aminoglycoside Antibiotic Mimetics:  Use of a Polyethylene Glycol-Linked Amine and a Neamine-Derived Aldehyde in Multiple Component Condensation as a Strategy for the Discovery of New Inhibitors of the HIV RNA Rev Responsive Element
  作者：William K. C. Park、Manfred Auer、Herbert Jaksche、Chi-Huey Wong

  DOI：10.1021/ja9612817

  日期：1996.1.1

  A library of neomycin B mimetics has been prepared rapidly without chromatography using a neamine-derived aldehyde, tert-butyl isocyanide or isocyanoacetic acid methyl ester, a glycine-conjugated polyethylene glycol (PEG) methyl ether, and various Cbz-N-protected amino acids as substrates in a Ugi-type one-pot reaction. The product linked to PEG was isolated by precipitation in ether. A simultaneous

  使用新霉素衍生的醛、叔丁基异氰化物或异氰乙酸甲酯、甘氨酸缀合的聚乙二醇 (PEG) 甲基醚和各种 Cbz-N 保护的氨基酸，无需色谱法即可快速制备新霉素 B 模拟物文库作为 Ugi 型一锅反应的底物。通过在乙醚中沉淀分离与PEG连接的产物。同时进行碱催化水解和脱氧乙酰化，然后进行氢化，可以轻松访问新霉素 B 模拟物库，该库已筛选与 HIV mRNA (RRE) 的 Rev 响应元件结合。发现一些产品比尼胺活性更高，IC50 值在微摩尔范围内。
• GLYCOAMINO ACID AND USE THEREOF
  申请人：AJINOMOTO CO., INC.

  公开号：US20170007709A1

  公开（公告）日：2017-01-12

  An object of the present invention is to provide an amino acid precursor which shows improvement in the properties (particularly water-solubility, stability in water, bitter taste etc.) of amino acid, and can be converted to amino acid in vivo etc. The present invention relates to a compound for an amino acid precursor, which is a compound represented by the formula (I): wherein each symbol is as described in the DESCRIPTION, or a salt thereof.

  本发明的目的是提供一种氨基酸前体，该前体在氨基酸的性质（特别是水溶性、在水中的稳定性、苦味等）方面表现出改进，并且可以在体内转化为氨基酸等。本发明涉及一种氨基酸前体化合物，该化合物由以下式（I）表示： 其中每个符号如描述中所述，或其盐。