Fmoc-L-天冬氨酸 4-烯丙酯 | 146982-24-3

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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: Fmoc-L-天冬氨酸 4-烯丙酯
• 中文别名: N-芴甲氧羰基-L-天冬氨酸4-烯丙酯；N-[(2-丙烯-1-基氧基)羰基]-L-天冬氨酸4-(9H-芴-9-基甲基)酯；Fmoc-L-天冬氨酸4-烯丙酯；N-芴甲氧羰基-L-天冬氨酸 4-烯丙酯；Fmoc-Asp(OAll)-OH
• 英文名称: N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester
• 英文别名: Fmoc-Asp(OAllyl)-OH；Fmoc-Asp-OAll；Fmoc-Asp(OAll)-OH；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-prop-2-enoxybutanoic acid；Fmoc-Asp(OAl)-OH；(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(allyloxy)-4-oxobutanoic acid；N-α-(9-fluorenylmethoxycarbonyl)-L-aspartic acid β-allyl ester；Fmoc-Asp(All)
• CAS: 146982-24-3
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: FBNFRRNBFASDKS-IBGZPJMESA-N

物化性质

• 熔点：
  111-115 °C
• 沸点：
  638.5±55.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)
• 溶解度：
  溶于水或1%醋酸

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 安全说明：
  S22
• WGK Germany：
  3
• 海关编码：
  2924 29 70
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-Asp(OAll)-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: Fmoc-Asp(OAll)-OH
CAS number: 146982-24-3

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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, refrigerated.
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: C22H21NO6
Molecular weight: 395.4

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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

制备方法与用途

用途

N-芴甲氧羰基-L-天冬氨酸4-烯丙酯是一种天冬氨酸衍生物，在医药和食品领域有着广泛的应用。

制备方法

1. 在三口瓶中，将四氢呋喃与天冬氨酸混合，然后在低温下滴加氧氯化磷。反应6小时后进行过滤，得到固体中间体。
2. 使用无水乙醚洗涤固体中间体，并烘干。随后将其与丙烯醇反应，在控制温度和时间的条件下完成反应，反应结束后用三乙胺调节pH值至7，促使固体析出。
3. 经过乙醚洗涤和干燥后，得到中间体L-Asp-0A11。
4. 将L-Asp-0A11溶解在碳酸氢钠溶液中，加入丙酮与Fmoc-0Su，并控制pH值约9，低温下反应3小时。
5. 反应完成后，用无水乙醚洗涤。通过醋酸乙酯进行产品提取，经过酸化、洗涤和干燥等步骤后浓缩至干。
6. 最终，使用石油醚结晶得到目标产物N-芴甲氧羰基-L-天冬氨酸4-烯丙酯。

反应信息

• 作为反应物：
  描述：

  Fmoc-L-天冬氨酸 4-烯丙酯 在 magnesium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到Fmoc-L-天冬氨酸
  参考文献：
  名称：

  MgI2介导的保护基团的化学选择性切割：常规脱保护方法的替代方法

  摘要：

  在此描述了MgI 2作为定量和轻度化学选择性切割保护基的有价值工具的范围。这种新颖的合成方法扩大了保护基的使用范围，拓宽了合成过程中正交性的概念，并提供了从固体载体上释放化合物的简便机会。

  DOI：

  10.1002/chem.201501799
• 作为产物：
  描述：

  Fmoc-Asp-(OAll)-OH 在 Alcalase-cross-linked-enzyme-aggregates 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 以77%的产率得到Fmoc-L-天冬氨酸 4-烯丙酯
  参考文献：
  名称：

  A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives

  摘要：

  Two versatile, high yielding, and efficient chemo-enzymatic methods for the synthesis of beta-protected Asp and gamma-protected Glu derivatives using Alcalase are described. The first method is based on the alpha-selective enzymatic hydrolysis of symmetrical aspartyl and glutamyl diesters. The second method involving mixed diesters comprises a three-step protocol using (i) alpha-selective enzymatic methyl-esterification, (ii) chemical beta-esterification, and finally (iii) alpha-selective enzymatic methyl ester hydrolysis. The yields of the purified beta- and gamma-esters range from 77% to 91%. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.130

文献信息

• [EN] DIRECTED CONJUGATION TECHNOLOGIES<br/>[FR] TECHNOLOGIES DE CONJUGAISON DIRIGÉE
  申请人：KLEO PHARMACEUTICALS INC

  公开号：WO2021102052A1

  公开（公告）日：2021-05-27

  Among other things, the present disclosure provides technologies for site-directed conjugation of various moieties of interest to target agents. In some embodiments, the present disclosure utilizes target binding moieties to provide high conjugation efficiency and selectivity. In some embodiments, provided technologies are useful for preparing antibody conjugates.

  本公开提供了用于将各种感兴趣的分子与目标剂进行定点偶联的技术。在某些实施方式中，本公开利用目标结合分子以提供高偶联效率和选择性。在某些实施方式中，所提供的技术可用于制备抗体偶联物。
• Dipeptidyl Peptidase IV Dependent Water-Soluble Prodrugs of Highly Lipophilic Bicyclic Nucleoside Analogues
  作者：Alberto Diez-Torrubia、Jan Balzarini、Graciela Andrei、Robert Snoeck、Ingrid De Meester、María-José Camarasa、Sonsoles Velázquez