N-[(1,1-二甲基乙氧基)羰基]-L-异亮氨酸甲酯 | 17901-01-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 异亮氨酸类衍生物
• 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: N-[(1,1-二甲基乙氧基)羰基]-L-异亮氨酸甲酯
• 中文别名: BOC-L-异亮氨酸甲酯
• 英文名称: N-(tert-butoxycarbonyl)isoleucine methyl ester
• 英文别名: N-(tert-butyloxycarbonyl)-L-isoleucine methyl ester；Boc-L-Ile-OMe；methyl (2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 17901-01-8
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: KLRYBAAAYDFIEQ-IUCAKERBSA-N

物化性质

• 沸点：
  322.5±25.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-Ile-OMe
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: Boc-Ile-OMe
CAS number: 17901-01-8

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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: C12H23NO4
Molecular weight: 245.3

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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-[(1,1-二甲基乙氧基)羰基]-L-异亮氨酸甲酯 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 ethyl (3R,4S,5S)-3-hydroxy-5-methyl-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]heptanoate
  参考文献：
  名称：

  A Synthetic Dolastatin 10 Analogue Suppresses Microtubule Dynamics, Inhibits Cell Proliferation, and Induces Apoptotic Cell Death

  摘要：

  We have synthesized eight analogues (D1-D8) of dolastatin 10 containing several unique amino acid subunits. Of these agents, D5 was found to be most effective in inhibiting both He La cell proliferation and microtubule assembly in vitro. At low nanomolar concentrations, 135 inhibited the proliferation of several types of cancer cells in culture. D5 bound to tubulin with a dissociation constant of 29.4 +/- 6 mu M. D5 depolymerized microtubules in cultured cells and produced mulitpolar spindles. At its half-maximal inhibitory concentration (15 nM), DS strongly suppressed the dynamics of individual microtubules in live MCF-7 cells. DS increased the accumulation of checkpoint proteins BubR1 and Mad2 at the kinetochoric region and caused G2/M block in these cells. The blocked cells underwent apoptosis with the activation of Jun N-terminal kinase. The results suggested that DS exerts its antiproliferative action by dampening microtubule dynamics.

  DOI：

  10.1021/jm3009629
• 作为产物：
  描述：

  methyl (2S,3S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-methylpentanoate 在 cerium(III) chloride 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 6.5h， 以92%的产率得到N-[(1,1-二甲基乙氧基)羰基]-L-异亮氨酸甲酯
  参考文献：
  名称：

  CeCl3·7H2O-NaI从氨基甲酸酯和酰胺中高效选择性裂解叔丁氧基羰基

  摘要：

  在环境温度和中性条件下，在乙腈中使用 CeCl 3 .7H 2 O-NaI 以高产率实现了叔丁氧基羰基的高度选择性裂解。该方法温和且与存在于基材中的多种官能团相容，例如THP、TBDMS、TBDPS、三苯甲基醚、单-BOC或Cbz保护的胺、乙酰胺、磺酰胺和苯甲酰胺等。

  DOI：

  10.1055/s-2002-20467

文献信息

• One-pot conversion of fluorenylmethyl carbamates into tert-butyl carbamates
  作者：Li Wen-Ren、Jiang Jianjun、Madeleine M. Joullié

  DOI：10.1016/s0040-4039(00)60305-2

  日期：1993.2

  N-Fluorenylmethoxycarbonyl groups may be efficiently converted into N-tert-butoxycarbonyl groups by pottassium flouride/Et3N in the presence of Boc2O

  在Boc 2 O存在下，氟化flour / Et 3 N可将N-氟烯基甲氧羰基有效地转化为N-叔丁氧羰基
• Synthesis, SAR and biological studies of sugar amino acid-based almiramide analogues: N-methylation leads the way
  作者：Dipendu Das、Hina P. A. Khan、Rahul Shivahare、Suman Gupta、Jayanta Sarkar、Mohd. Imran Siddiqui、Ravi Sankar Ampapathi、Tushar Kanti Chakraborty

  DOI：10.1039/c6ob02610a

  日期：——

  Leishmania, is one of the most neglected diseases endemic in many continents posing enormous global health threats and therefore the discovery of new antileishmanial compounds is of utmost urgency. The antileishmanial activities of a library of sugar amino acid-based linear lipopeptide analogues were examined with the aim to identify potential drug candidates to treat visceral leishmaniasis. It was

  由利什曼原虫属的原生动物寄生虫引起的利什曼病是许多大陆上流行最严重的被忽视的疾病之一，对全球健康构成了巨大的威胁，因此，迫切需要发现新的动物抗疟疾化合物。检查了基于糖氨基酸的线性脂肽类似物库的抗菌活性，目的是鉴定潜在的候选药物治疗内脏利什曼病。已经发现，在合成的类似物中，大多数全甲基化的化合物在体外研究中显示出比非甲基化的类似物更强的抗巨噬细胞内变形虫的活性。SAR和NMR研究表明N的引入-甲基基团抑制了这些分子中任何转向结构的形成，从而改善了它们的活性。
• Cyclopeptide Alkaloids from <i>Paliurus </i><i>r</i><i>amossisimus</i>
  作者：Hui-yi Lin、Chung-Hsiung Chen、Bih-Jing You、Karin C. S. Chen Liu、Shoei-Sheng Lee

  DOI：10.1021/np000136a

  日期：2000.10.1

  Seven zizyphine A-type cyclopeptide alkaloids were isolated from the roots of Paliurus ramossisimus by the combination of centrifugal partition chromatography and conventional separation methods. The novel structures of paliurines A-F (1-6) were characterized and established on the basis of MS and elaborate NMR spectral analyses. Terminal dipeptide stereochemistry was confirmed by correlation with

  通过离心分配色谱法和常规分离方法相结合，从七叶锦葵的根中分离出七个子碱A型环肽生物碱。在MS和精细的NMR光谱分析的基础上，对并构造了新的结构的paliurines AF（1-6）。通过比较合成的二肽的（13）C NMR数据，证实了其末端二肽的立体化学。
• Synthesis, Biological Evaluation, and Molecular Modeling Studies of Chiral Chloroquine Analogues as Antimalarial Agents
  作者：Srinivasarao Kondaparla、Utsab Debnath、Awakash Soni、Vasantha Rao Dola、Manish Sinha、Kumkum Srivastava、Sunil K. Puri、Seturam B. Katti

  DOI：10.1128/aac.02347-17

  日期：2018.12

  quantitative structure-activity relationship (3D-QSAR) studies of all in-house data sets (168 molecules) of chiral CQ analogues to explain the structure-activity relationships (SAR). Our new findings specify the significance of the H-bond interaction with the side chain of heme for biological activity. In addition, the 3D-QSAR study against the 3D7 strain indicated the favorable and unfavorable sites

  在重点研究中，我们设计，合成和生物评估了手性共轭新氯喹（CQ）类似物，并用取代的哌嗪作为抗疟剂。体外和体内研究表明，化合物7c表现出有效的活性（体外50％抑制浓度，菌株3D7的抑制浓度为56.98 nM，菌株K1的抑制浓度为97.76 nM；在体内的选择性指数[最高剂量为12.5 mg / kg [体重]，3,510）作为新型抗疟药物。其他化合物（化合物6b，6d，7d，7h，8c，8d，9a和9c）也显示出对CQ敏感菌株（3D7）的中等活性，并且对恶性疟原虫的CQ抗性菌株（K1）的活性更高。 ，我们对手性CQ类似物的所有内部数据集（168个分子）进行了对接和三维定量构效关系（3D-QSAR）研究，以解释构效关系（SAR）。我们的新发现指定了与血红素侧链的H键相互作用对生物活性的重要性。此外，针对3D7菌株的3D-QSAR研究表明，CQ类似物的有利位置和不利位置会引入空间，疏水和正电基团，以提高抗疟活性。
• Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids
  作者：Yuan Ji、Jessica Sweeney、Jillian Zoglio、David J. Gorin

  DOI：10.1021/jo401941v

  日期：2013.11.15

  Although methylation reactions are commonplace, currently used reagents are hazardous, toxic, and/or unstable. Dimethylcarbonate has been put forth as an inexpensive, nontoxic, and “green” potential methylating reagent. Herein we report a general, base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids. High selectivity for esterification is observed even in the presence of unprotected

  尽管甲基化反应很普遍，但是当前使用的试剂是危险的，有毒的和/或不稳定的。碳酸二甲酯已被提出为廉价，无毒且“绿色”的潜在甲基化试剂。本文中，我们报道了一般的碱催化的甲基碳酸酯从碳酸二甲酯向羧酸的转移。即使在未保护的苯酚存在下，也观察到了对酯化的高选择性，温和的反应条件使在可差向立体中心处的立体化学得以保留。同位素标记研究表明，机制是通过将甲基直接从碳酸二甲酯转移到底物上来进行的。