N-Fmoc-N-甲基-L-苏氨酸 | 252049-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-Fmoc-N-甲基-L-苏氨酸
• 中文别名: N-[芴甲氧羰基]-N-甲基-L-苏氨酸
• 英文名称: N-Fmoc-N-methyl-L-threonine
• 英文别名: Fmoc-N-methyl-threonine；Fmoc-N-Me-Thr-OH；(2S,3R)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-hydroxybutanoic acid
• CAS: 252049-06-2
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: YBKRZKSVPNEMQK-XIKOKIGWSA-N

物化性质

• 沸点：
  566.4±50.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-n-me-thr-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-n-me-thr-oh
CAS number: 252049-06-2

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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: C20H21NO5
Molecular weight: 355.4

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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-Fmoc-N-甲基-L-苏氨酸 在 哌啶 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.17h， 生成 (5S)-4-(benzyloxy)-1-methyl-5-{(1R)-1-[(triisopropylsilyl)oxy]ethyl}-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2

  摘要：

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.116
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl (4S)-4-[(1R)-1-acetyloxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate 在 盐酸 、 三乙基硅烷 、 aluminum (III) chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 N-Fmoc-N-甲基-L-苏氨酸
  参考文献：
  名称：

  Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2

  摘要：

  The Penicillium metabolites penicillenols B-1 and B-2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an L-threonine derived tetramic acid. The (Z,S)-and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B-1 was also notably antibiotic against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.116

文献信息

• Solid-Phase Total Synthesis of the Proposed Structure of Coibamide A and Its Derivative: Highly Methylated Cyclic Depsipeptides
  作者：Ganesh A. Sable、Jaekwan Park、Hyunsik Kim、Soo-Jeong Lim、Soonmin Jang、Dongyeol Lim

  DOI：10.1002/ejoc.201500697

  日期：2015.11

  The solid-phase total synthesis of the proposed structure of cyclic depsipeptide coibamide A and its derivative O-desmethyl coibamide A is reported. In this study, we demonstrate the solid-phase synthetic strategy and final solution-phase O-methylation for highly N-methylated cyclic depsipeptides. On-resin macrocyclization, N,N-dimethylation and solution-phase O-methylation were the key steps of these

  报道了环状缩酚酚醛酰胺 A 及其衍生物 O-去甲基 coibamide A 的拟议结构的固相全合成。在这项研究中，我们展示了高度 N-甲基化环状缩肽的固相合成策略和最终溶液相 O-甲基化。树脂上大环化、N,N-二甲基化和液相O-甲基化是这些合成的关键步骤。根据液相色谱-质谱 (LCMS) 分析，合成 coibamide A 的质量与天然产物的质量一致，但在 1H 和 13C NMR 分析中观察到显着差异。
• A new GLP-1 analogue with prolonged glucose-lowering activity in vivo via backbone-based modification at the N-terminus
  作者：Xiaohui Bai、Youhong Niu、Jingjing Zhu、An-Qi Yang、Yan-Fen Wu、Xin-Shan Ye

  DOI：10.1016/j.bmc.2016.01.036

  日期：2016.3

  Glucagon-like peptide-1 (GLP-1) is an endogenous insulinotropic hormone with wonderful glucose-lowering activity. However, its clinical use in type II diabetes is limited due to its rapid degradation at the N-terminus by dipeptidyl peptidase IV (DPP-IV). Among the N-terminal modifications of GLP-1, backbone-based modification was rarely reported. Herein, we employed two backbone-based strategies to modify the N-terminus of tGLP-1. Firstly, the amide N-methylated analogues 2-6 were designed and synthesized to make a full screening of the N-terminal amide bonds, and the loss of GLP-1 receptor (GLP-1R) activation indicated the importance of amide H-bonds. Secondly, with retaining the N-terminal amide H-bonds, the beta-peptide replacement strategy was used and analogues 7-13 were synthesized. By two rounds of screening, analogue 10 was identified. Analogue 10 greatly improved the DPP-IV resistance with maintaining good GLP-1R activation in vitro, and showed approximately a 4-fold prolonged blood glucose-lowering activity in vivo in comparison with tGLP-1. This modification strategy will benefit the development of GLP-1-based anti-diabetic drugs. (C) 2016 Elsevier Ltd. All rights reserved.
• An improved synthesis of Fmoc-N-methyl serine and threonine
  作者：Rajesh H. Bahekar、Pradip A. Jadav、Dipam N. Patel、Vijay M. Prajapati、Arun A. Gupta、Mukul R. Jain、Pankaj R. Patel

  DOI：10.1016/j.tetlet.2007.05.112

  日期：2007.7

  An improved method for the synthesis of Fmoc-N-methyl serine and threonine has been developed, which involves formation and subsequent reduction of the corresponding oxazolidinone with a Lewis acid under mild conditions, with improved yields and shorter reaction times. (C) 2007 Elsevier Ltd. All rights reserved.