Fmoc-O-三苯甲基-L-苏氨酸 | 133180-01-5

• 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 - 三苯基化合物
• 中文名称: Fmoc-O-三苯甲基-L-苏氨酸
• 中文别名: N-芴甲氧羰基-O-三苯甲基-L-苏氨酸；NΑ-(9-芴甲氧羰酰基)-O-三苯甲基-L-苏氨酸；FMOC-O-三苯甲基-L-苏氨酸
• 英文名称: Fmoc-O-trityl-l-threonine
• 英文别名: Fmoc-Thr(Trt)-OH；N-Fmoc-O-trityl-L-threonine；(2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-trityloxybutanoic acid
• CAS: 133180-01-5
• 化学式: C₃₈H₃₃NO₅
• 分子量: 583.684
• InChiKey: JARBLLDDSTVWSM-IJAHGLKVSA-N

物化性质

• 沸点：
  753.0±60.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封，在-20°C下保存

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-thr(trt)-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-thr(trt)-oh
CAS number: 133180-01-5

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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: C38H33NO5
Molecular weight: 583.7

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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

N-((9H-芴-9-基)甲氧基)羰基)-O-三烷基-L-三氢嘌呤是一种苏氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  Fmoc-O-三苯甲基-L-苏氨酸 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 Nα-[(9H-芴-9-基甲氧基)羰基]-L-苏氨酸叔丁酯
  参考文献：
  名称：

  固相肽合成的笼状磷酸氨基酸构件。

  摘要：

  已经合成了三种1-（2-硝基苯基）乙基笼罩的磷酸氨基酸，用于标准的基于Nα-芴基甲氧基羰基的固相肽合成（SPPS）。通过使用独特的磷酸化试剂进行修饰，可将最常见的天然磷酸氨基酸，丝氨酸，苏氨酸和酪氨酸制成受保护的笼状结构单元。在先前的工作中，使用相互组装的方法制备了笼状磷酸肽（Rothman，DM； Vazquez，ME； Vogel，EM； Imperiali，B.Org.Lett.2002，4，2865-2868）。然而，该技术限于产生不具有要修饰的氨基酸的C末端的氧化敏感残基的肽，并且该方法涉及在固相上的合成操作，这可能会限制该方法的利用。

  DOI：

  10.1021/jo0344891
• 作为产物：
  描述：

  三苯基氯甲烷 在 4-二甲氨基吡啶 、 sodium hydroxide 、 2,2,2-三氟乙醇 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 Fmoc-O-三苯甲基-L-苏氨酸
  参考文献：
  名称：

  N-Fmoc-O-Trt-hydroxyaminosäurenzur“固相”合成冯肽

  摘要：

  The preparation of the N-Fmoc-O-Trt derivatives of serine, threonine and tyrosine is described. Their usefulness in peptide synthesis has been determined in the successful solid phase preparation of the partially protected ACTH (fragment 1-10) and peptide T 12. The latter, having six hydroxy amino acid side chains protected with Trt groups, can be quantitatively cleaved from the applied 2-chlorotrityl resin with simultaneous side chain deprotection.

  DOI：

  10.1016/s0040-4039(00)79471-8

文献信息

• Structure−Activity Relationship Studies Optimizing the Antiproliferative Activity of Novel Cyclic Somatostatin Analogues Containing a Restrained Cyclic β-Amino Acid
  作者：Martin Sukopp、Richard Schwab、Luciana Marinelli、Eric Biron、Markus Heller、Edit Várkondi、Ákos Pap、Ettore Novellino、György Kéri、Horst Kessler

  DOI：10.1021/jm049500j

  日期：2005.4.1

  The cyclic somatostatin analogue cyclo[Pro(1)-Phe(2)-D-Trp(3)-Lys(4)-Thr(5)-Phe(6)] (L-363,301) displays high biological activity in inhibiting the release of growth hormone, insulin, and glucagon. According to the sequence of L-363,301, we synthesized a number of cyclic hexa- and pentapeptides containing nonnatural alpha- and beta-amino acids. The N- fluorenylmethoxycarbonyl protected cyclic beta-amino

  环状生长抑素类似物环[Pro（1）-Phe（2）-D-Trp（3）-Lys（4）-Thr（5）-Phe（6）]（L-363,301）在抑制细胞生长方面表现出高生物活性。释放生长激素，胰岛素和胰高血糖素。根据L-363,301的序列，我们合成了许多含有非天然α-和β-氨基酸的环状六肽和五肽。N-芴基甲氧基羰基保护的环状β-氨基酸[1S，2S，5R] -2-氨基-3,5-二甲基-2-环己-3-烯基羧酸（cbetAA ），用于取代Phe（6）- L-363,301的Pro（1）部分是使用（-）-8-苯基薄荷醇作为手性助剂，通过对映选择性多组分反应分两步合成的。所得的肽环[cbetAA （1）-Tyr（2）-D-Trp（3）-Nle（4）-Thr（Trt）（5）]（Trt =三苯甲基）在具有A431癌细胞。没有Trt基团的相同肽没有显示任何生物学活性，而L-363,301和紧密相关的六肽仅显示了较
• Development of oxetane modified building blocks for peptide synthesis
  作者：Stefan Roesner、Jonathan D. Beadle、Leo K. B. Tam、Ina Wilkening、Guy J. Clarkson、Piotr Raubo、Michael Shipman

  DOI：10.1039/d0ob01208d

  日期：——

  The synthesis and use of oxetane modified dipeptide building blocks in solution and solid-phase peptide synthesis (SPPS) is reported. The preparation of building blocks containing non-glycine residues at the N-terminus in a stereochemically controlled manner is challenging. Here, a practical 4-step route to such building blocks is demonstrated, through the synthesis of dipeptides containing contiguous

  报道了在溶液和固相肽合成（SPPS）中氧杂环丁烷修饰的二肽结构单元的合成和使用。以立体化学控制的方式制备在N端含有非甘氨酸残基的结构单元是具有挑战性的。在此，通过合成包含连续丙氨酸残基的二肽，证明了通向此类结构单元的实际4步路线。这些新衍生物在包含18个氨基酸的富含丙氨酸的肽序列的骨架的特定位点上的掺入通过固相肽合成。另外，通过改变合成路线（对于Cys和Met）和改变保护基的策略（对于His，Ser和Thr），报道了使所有20个蛋白原氨基酸都可以掺入这种二肽构件的新方法。 ）。
• [EN] CONJUGATES OF TACROLIMUS, THEIR COMPOSITIONS, AND THEIR USES<br/>[FR] CONJUGUÉS DE TACROLIMUS, LEURS COMPOSITIONS ET LEURS UTILISATIONS
  申请人：THE ADMINISTRATORS OF THE TULANE EDUCATIONAL FUND

  公开号：WO2017165607A1

  公开（公告）日：2017-09-28

  Some embodiments of the invention include inventive compounds (e.g., compounds of Formula (I)) including but not limited to conjugates comprising FK-506 and ascomycin. Other embodiments include compositions (e.g., pharmaceutical compositions) comprising the inventive compound. Still other embodiments of the invention include compositions for treating, for example, certain diseases using the inventive compounds. Some embodiments include methods of using the inventive compound (e.g., in compositions or in pharmaceutical compositions) for administering and treating. Further embodiments include methods for making the inventive compound. Additional embodiments of the invention are also discussed herein.

  本发明的某些实施例包括创新化合物（例如，公式（I）的化合物），包括但不限于包含FK-506和ascomycin的缀合物。其他实施例包括由创新化合物组成的组合物（例如，药物组合物）。本发明的进一步实施例包括用于治疗某些疾病的组合物，例如，使用创新化合物。一些实施例包括使用创新化合物的方法（例如，在组合物中或药物组合物中）用于给药和治疗。进一步的实施例包括制造创新化合物的方法。本发明还讨论了其他的实施例。
• A Convenient, General Synthesis of 1,1-Dimethylallyl Esters as Protecting Groups for Carboxylic Acids
  作者：Minoo Sedighi、Mark A. Lipton

  DOI：10.1021/ol0476117

  日期：2005.4.14

  1-dimethylallyl (DMA) esters in two steps. Palladium-catalyzed deprotection of DMA esters was shown to be compatible with tert-butyl, benzyl, and Fmoc protecting groups, and Fmoc deprotection could be carried out selectively in the presence of DMA esters. DMA esters were also shown to be resistant to nucleophilic attack, suggesting that they will serve as alternatives to tert-butyl esters when acidic deprotection

  [反应：请参见文本]通过两步将羧酸高收率转化为其1,1-二甲基烯丙基（DMA）酯。钯催化的DMA酯的脱保护显示与叔丁基，苄基和Fmoc保护基相容，并且Fmoc的脱保护可以在DMA酯存在下选择性进行。DMA酯还显示出对亲核攻击的抵抗力，这表明当需要避免酸性脱保护条件时，它们可作为叔丁基酯的替代品。
• Cu-Catalyzed Asymmetric Allylic Alkylations of Aromatic and Aliphatic Phosphates with Alkylzinc Reagents. An Effective Method for Enantioselective Synthesis of Tertiary and Quaternary Carbons
  作者：Monica A. Kacprzynski、Amir H. Hoveyda

  DOI：10.1021/ja0478779

  日期：2004.9.1

  Efficient enantioselective Cu-catalyzed allylic alkylations of aromatic and aliphatic allylic phosphates bearing di- and trisubstituted olefins are disclosed. Enantioselective C-C bond forming reactions are promoted in the presence of 10 mol % readily available chiral amino acid-based ligand (5 steps, 40% overall yield synthesis) and 5 mol % (CuOTf)2 x C6H6. Reactions deliver tertiary and quaternary stereogenic

  公开了带有二和三取代烯烃的芳族和脂族烯丙基磷酸酯的有效对映选择性Cu催化的烯丙基烷基化。在 10 mol% 容易获得的手性氨基酸基配体（5 步，40% 总产率合成）和 5 mol% (CuOTf)2 x C6H6 存在下，对映选择性 CC 键形成反应得到促进。反应区域选择性地以 78-96% ee 传递叔和四元立体碳中心。提供了有关配体结构变化对烷基化过程的效率和对映选择性的影响的数据，以及机械工作模型。建议的模型涉及手性 Cu 络合物的双重作用：Cu(I) 中心与烯烃的结合是通过配体羰基之间的两点结合来促进的