Z-O-叔丁基-D-丝氨酸 | 65806-90-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Z-O-叔丁基-D-丝氨酸
• 中文别名: N-苄氧羰基-O-叔丁基-D-丝氨酸
• 英文名称: (R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoic acid
• 英文别名: (R)-2-(benzyloxycarbonylamino)-3-tert-butoxypropanoic acid；N-benzyloxycarbonyl-O-t-butyl-D-serine；Z-D-Ser(Bu^t)-OH；Z-D-Ser(tBu)-OH；Z-D-Ser(OtBu)；Z-DSer(tBu)；(2R)-3-[(2-methylpropan-2-yl)oxy]-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 65806-90-8
• 化学式: C₁₅H₂₁NO₅
• mdl: MFCD00077038
• 分子量: 295.335
• InChiKey: TXDGEONUWGOCJG-GFCCVEGCSA-N

物化性质

• 沸点：
  465.3±45.0 °C(Predicted)
• 密度：
  1.174±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)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.466
• 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,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-D-Ser(tbu)-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: Z-D-Ser(tbu)-OH
CAS number: 65806-90-8

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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.
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: C15H21NO5
Molecular weight: 295.3

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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：

  Z-O-叔丁基-D-丝氨酸 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 sodium hydride 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， -20.0~20.0 ℃ 、101.33 kPa 条件下， 反应 20.17h， 生成
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS FOR MODULATION OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (ROR? GAMMA, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASE
  [FR] NOUVEAUX COMPOSÉS POUR MODULATION DE L'ACTIVITÉ RÉCEPTEUR GAMMA ORPHELIN ASSOCIÉ AU RÉCEPTEUR NUCLÉAIRE ORPHELIN RAR (RORG GAMMA, NR1F3) ET POUR LE TRAITEMENT D'UNE MALADIE INFLAMMATOIRE ET AUTO-IMMUNE CHRONIQUE

  摘要：

  该发明提供了用于孤儿核受体RORγ的调节剂，以及通过将这些新型RORγ调节剂用于需要的人类或哺乳动物治疗RORγ介导疾病的方法。具体而言，本发明提供了Formula (1)的化合物及其对映体、顺式异构体、互变异构体、溶剂合物和药用可接受盐。

  公开号：

  WO2011107248A1
• 作为产物：
  描述：

  O-(叔丁基)-N-[苄氧羰基]-D-丝氨酸甲酯 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.67h， 以88%的产率得到Z-O-叔丁基-D-丝氨酸
  参考文献：
  名称：

  Masiukiewicz, E.; Rzeszotarska, B.; Wiejak, S., Polish Journal of Chemistry, 1995, vol. 69, # 5, p. 674 - 680

  摘要：

  DOI：

文献信息

• New Oxazole-Based Peptidomimetics:  Useful Building Blocks for the Synthesis of Orthogonally Protected Macrocyclic Scaffolds
  作者：Enrique Mann、Horst Kessler

  DOI：10.1021/ol035673b

  日期：2003.11.1

  [structure: see text] The synthesis of a new family of densely functionalized oxazole-containing amino acids is described. These building blocks were employed for preparing macrocycles containing Lys and Glu residues by a combination of solid- and solution-phase synthesis. The resulting structures are presented as orthogonally protected scaffolds for supramolecular chemistry.

  [结构：见正文]描述了新的致密官能化的含恶唑氨基酸家族的合成。这些结构单元被用于通过固相和溶液相合成的组合来制备含有Lys和Glu残基的大环化合物。所得的结构作为用于超分子化学的正交保护的支架存在。
• [EN] DNA POLYMERASE THETA INHIBITORS<br/>[FR] INHIBITEURS DE L'ADN POLYMÉRASE THÊTA
  申请人：ARTIOS PHARMA LTD

  公开号：WO2021123785A1

  公开（公告）日：2021-06-24

  The invention relates to heterocyclic derivatives and their use in the treatment and prophylaxis of cancer, and to compositions containing said derivatives and processes for their preparation.

  这项发明涉及杂环衍生物及其在癌症治疗和预防中的应用，以及含有这些衍生物的组合物和它们的制备方法。
• [EN] SEVEN-MEMBERED SULFONAMIDES AS MODULATORS OF RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORgamma, NR1F3)<br/>[FR] SULFONAMIDES À SEPT CHAÎNONS COMME MODULATEURS DES RÉCEPTEURS GAMMA ORPHELINS ASSOCIÉS À UN RÉCEPTEUR DE L'ACIDE RÉTINOÏQUE (RORGamma, NR1F3)
  申请人：PHENEX PHARMACEUTICALS AG

  公开号：WO2013064231A1

  公开（公告）日：2013-05-10

  The invention provides modulators for the orphan nuclear receptor RORγ and methods for treating RORγ mediated diseases by administration of these novel RORγ modulators to a human or a mammal in need thereof. Specifically, the present invention provides compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof as well as pharmaceutical compositions comprising said compounds as an active ingredient.

  这项发明提供了孤儿核受体RORγ的调节剂，以及通过向需要治疗RORγ介导疾病的人类或哺乳动物施用这些新型RORγ调节剂的方法。具体而言，本发明提供了式（1）的化合物及其对映体、二对映体、互变异构体、溶剂化合物和药学上可接受的盐，以及包含所述化合物作为活性成分的药物组合物。
• Syntheses of Triostin A Antibiotic and Nucleobase-Functionalized Analogs as New DNA Binders
  作者：Anmol Kumar Ray、Ulf Diederichsen

  DOI：10.1002/ejoc.200900530

  日期：2009.10

  The attachment of functional units was achieved by the orthogonal protection of the respective side chain amino functionalities. The nucleobase-functionalized triostin analogs have the potential to recognize double-stranded DNA by hydrogen bonding. The interaction with DNA was investigated by UV spectroscopy and fluorescence intercalator displacement. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  描述了天然产物 Triostin A 的全合成，其中 N-甲基化缩肽支架是通过溶液相肽化学构建的，然后是二硫化物形成和大环化。最后，连接喹喔啉以提供 DNA 双嵌入剂。Triostin A 的类似物是通过用嘧啶或嘌呤识别单元对环状缩酚肽进行连续功能化而获得的。功能单元的连接是通过相应侧链氨基官能团的正交保护来实现的。核碱基功能化的 Triostin 类似物具有通过氢键识别双链 DNA 的潜力。通过紫外光谱和荧光嵌入剂置换研究了与 DNA 的相互作用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,
• Synthetic Studies on Quinoxaline Antibiotics. II. Synthesis of Triostin A
  作者：Masaru Shin、Ken Inouye、Hideo Otsuka

  DOI：10.1246/bcsj.57.2203

  日期：1984.8

  Triostin A, a cyclic octadepsipeptide, was synthesized with Z–D-Ser[Boc–Ala–MeCys(Bzl)–MeVal]–OH and Z–D-Ser[H–Ala–MeCy(Bzl)–MeVal]–OTce as key intermediates. The synthetic antibiotic was compared with natural triostin A in terms of chromatographic behaviors, NMR spectra, and antimicrobial activity to establish their identity. The NMR data on S,S′-dibenzyldihydrotriostin A showed that this intermediate

  Triostin A，一种环状十八肽，由 Z-D-Ser[Boc-Ala-MeCys(Bzl)-MeVal]-OH 和 Z-D-Ser[H-Ala-MeCy(Bzl)-MeVal]-OTce 合成为关键中间体。在色谱行为、核磁共振谱和抗菌活性方面将合成抗生素与天然曲奥斯汀 A 进行比较，以确定它们的身份。S,S'-dibenzyldihydrotriostin A 的 NMR 数据表明，这种缺乏二硫键的中间体在氯仿中也以两个构象异构体的形式存在。这一观察结果排除了已知与 Triostin A 发生的构象平衡是二硫键反向手性的结果的可能性。