N-(苄氧羰基)-L-酪氨酸苄酯 | 5513-40-6

• 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: N-(苄氧羰基)-L-酪氨酸苄酯
• 中文别名: 苄氧羰基-酪氨酸-苄酯
• 英文名称: benzyl N-carbobenzyloxy-L-tyrosine
• 英文别名: (S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate；Cbz-L-Tyrosine benzyl ester；benzyl (2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 5513-40-6
• 化学式: C₂₄H₂₃NO₅
• 分子量: 405.45
• InChiKey: MUSDDUICYXQXRT-QFIPXVFZSA-N

物化性质

• 沸点：
  610.8±55.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 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：
  存储条件：2-8°C，干燥密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Cbz-L-Tyrosine benzyl ester
Synonyms: Z-L-Tyrosine benzyl ester; (S)-Benzyl 2-(benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propanoate

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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: Cbz-L-Tyrosine benzyl ester
CAS number: 5513-40-6

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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: C24H23NO5
Molecular weight: 405.4

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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-(苄氧羰基)-L-酪氨酸苄酯 在 palladium diacetate 、 palladium on activated charcoal 2,6-二甲基吡啶 、 1,1'-双(二苯基膦)二茂铁 、 三氟化硼乙醚 、 氢气 、 potassium acetate 、 sodium carbonate 作用下， 以 二氯甲烷 、 环己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 FMOC-p-羧基-Phe(OtBu)-OH
  参考文献：
  名称：

  用于基于Fmoc的固相肽合成的4-羧基苯丙氨酸及其衍生物的立体定向合成

  摘要：

  获得N α -苄氧羰基-L-酪氨酸（ø -三氟甲基）苄基酯，我们准备了使用钯（0）催化的羰基化反应对映体纯的4- carboxyphenylalanine和4- methoxycarbonylphenylalanine衍生物。这些非天然氨基酸被适当地保护，并用于使用Fmoc /叔丁基方法的固相肽合成中。

  DOI：

  10.1016/s0040-4039(96)01490-6
• 作为产物：
  描述：

  L-酪氨酸 在 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 15.0h， 生成 N-(苄氧羰基)-L-酪氨酸苄酯
  参考文献：
  名称：

  Phosphorylation of Tyrosine and Tyr-Thr-Lys Tripeptide with Cyclohexylmethyl- and (Deuteromethyl)phosphonochloridates

  摘要：

  Methods for phosphorylation of tyrosine and Tyr-Thr-Lys tripeptide with cyclohexylmethyl(deuteromethyl)phosphonochloridates have been developed. These products can be used as reference compounds in the analysis of blood plasma of patients presumably exposed to cyclohexylmethylphosphonofluoridate (cyclosarin) action. Conditions for the separation and purification of the synthesized intermediates by means of chromatography have been determined and optimized, allowing high-purity phosphorylated products at the final stage of the synthesis.

  DOI：

  10.1134/s1070363220040106

文献信息

• Stereoselektive Glycosylierung von Steroidalkoholen mit 2,3,4,6-Tetra-O-privaloyl-α-D-glucopyranosylbromid (Pivalobromglucose) und 2,3,4,6-Tetra-O-(o-toluoyl)-α-D-glucopyranosylbromid
  作者：Albrecht Harreus、Horst Kunz

  DOI：10.1002/jlac.198619860411

  日期：1986.4.15

  elektronischen und sterischen Gründen in ihrer Reaktivität differieren und die darüber hinaus empfindliche Gruppierungen enthalten, werden mit 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosylbromid (1) selektiv und effektiv in β-Glucoside übergeführt. Dank des lenkenden Einflusses des 2-O-Pivaloyl-Substituenten wird eine Orthoesterbildung bei den Koenigs-Knorr-Reaktionen stark unterdrückt. Mit dem o-Toluoylrest

  各种结构的甾醇，其羟基官能团由于电子和空间原因而具有不同的反应性，并且还包含敏感基团，它们对2,3,4,6 - tetra - O - pivaloyl -α-D-具有选择性并有效吡喃葡萄糖基溴化物（1）转化为β-葡萄糖苷。由于2- O-新戊酰基取代基的直接影响，在Koenigs-Knorr反应中原酸酯的形成被强烈抑制。用邻甲苯甲酰基作为羟基保护基，这种控制只能在很小的程度上实现。
• A New Utility of<i>O</i>-Glycosylpseudoureas for Synthesis of Glucopeptides and (1 → 6)-Disaccharides
  作者：Štefica Horvat、Lidija Varga、Jaroslav Horvat

  DOI：10.1055/s-1986-31617

  日期：——

  The synthetic utility of O-glycosylpseudourea derivatives for the preparation of glucosyl ethers and esters of amino acids and peptides (5, 6), and (1 → 6)- disaccharides (8) is reported. Simple two-step transformation of 1-O-unprotected sugars 1 is accomplished by a one-pot procedure giving products with high stereoselectivity in some cases.

  报道了O-糖苷伪尿素衍生物在制备氨基酸和肽的葡萄糖苷醚及酯（5, 6）以及（1 → 6）二糖（8）方面的合成应用。通过一种一锅法完成了1-O未保护糖1的简单两步转化，在某些情况下产品具有高立体选择性。
• Asymmetric Michael addition of malonates to enones catalyzed by a siloxy amino acid lithium salt
  作者：Masanori Yoshida、Mao Narita、Keisuke Hirama、Shoji Hara

  DOI：10.1016/j.tetlet.2009.10.033

  日期：2009.12

  Siloxy amino acid lithium salt, O-tert-butyldiphenylsilyl l-serine lithium salt, was found to be an effective catalyst for the asymmetric Michael addition reaction of malonates to enones.

  甲硅烷氧基氨基酸锂盐，ö -叔-butyldiphenylsilyl升丝氨酸锂盐，被认为是对于丙二酸酯的不对称迈克尔加成反应烯酮的有效催化剂。
• Polypeptides. Part XII. The preparation of 2-pyridyl esters and their use in peptide synthesis
  作者：A. S. Dutta、J. S. Morley

  DOI：10.1039/j39710002896

  日期：——

  amino-acid derivatives, and hydroxy-compounds) than the corresponding p-nitrophenyl esters. Evidence is presented that they are likely to be particularly useful in solid-phase peptide synthesis, and in the synthesis of O-peptides and depsipeptides.

  2-吡啶基的酯ñ -酰基氨基羧酸可从羧酸，2-羟基吡啶，并准备NN（仅“在吡啶-dicyclohexylcarbodi酰亚胺ñ在乙腈或二氯甲烷中形成-acylureas）。所述Ñ -t丁氧基-羰基-氨基甲酸2-吡啶基酯是大多结晶的，稳定的，并且在非极性溶剂相当对亲核试剂（胺，氨基-酯和酰胺更具反应性的，受阻氨基酸衍生物，和羟基化合物）比相应的对硝基苯酯。证据表明，它们可能在固相肽合成以及O肽和depsipeptide的合成中特别有用。
• Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions
  作者：Chun‐Wei Chang、Mei‐Huei Lin、Chieh‐Kai Chan、Kuan‐Yu Su、Chia‐Hui Wu、Wei‐Chih Lo、Sarah Lam、Yu‐Ting Cheng、Pin‐Hsuan Liao、Chi‐Huey Wong、Cheng‐Chung Wang

  DOI：10.1002/anie.202013909

  日期：2021.5.25

  (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure

  糖基化反应的立体选择性和产率至关重要，但不可预测。我们已经开发了一个亲核亲核常数（Aka）数据库，用于量化受空间，电子和结构效应影响的糖基化中羟基的亲核性，从而在实验和计算机算法之间建立联系。各种碳水化合物分子上的羟基之间的细微反应性差异可以由Aka定义，Aka可以通过简单便捷的自动化系统轻松访问，以确保高重现性和准确性。通过设计的软件程序“ GlycoComputer”可以组织和处理各种具有明确反应性和启动子的糖基化供体和受体，从而无需复杂的计算过程即可预测糖基化反应。通过随机森林算法进一步验证了Aka的重要性，并通过合成Lewis A骨架测试了适用性，表明可以准确估计立体选择性和产率。