(S)-3-amino-2-tert-butoxycarbonylaminopropionic acid | 76387-70-7

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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
• 英文名称: (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid
• 英文别名: (S)-3-amino-2-((tert-butoxycarbonyl)amino)propanoic acid；Boc-Dap-OH；(2S)-3-amino-2-(tert-butoxycarbonylamino)propanoic acid；Boc-L-2,3-diaminopropionic acid；Boc-L-Dap-OH；Nα-tert-butyloxycarbonyl-L-2,3-diaminopropionic acid；Nα-tert-butoxycarbonyl-L-2,3-diaminopropionic acid；3-amino-N-Boc-L-alanine；(2S)-3-ammonio-2-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]propanoate；(2S)-3-azaniumyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 76387-70-7
• 化学式: C₈H₁₆N₂O₄
• mdl: MFCD00236843
• 分子量: 204.226
• InChiKey: KRJLRVZLNABMAT-YFKPBYRVSA-N

物化性质

• 熔点：
  200-203℃
• 沸点：
  364.4±37.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  29225090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应存放在室温、密封和干燥的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Boc-D-Dap-OH
Product Name:
Synonyms: (R)-3-Amino-Boc-Alanine

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Boc-D-Dap-OH
Ingredient name:
CAS number: 76387-70-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H16N2O4
Molecular weight: 204.2

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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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 20.0 ℃ 、551.59 kPa 条件下， 反应 39.58h， 生成 tert-butyl (2S)-3-amino-2-(tert-butoxycarbonylamino)propanoate
  参考文献：
  名称：

  [EN] THERAPEUTIC COMPOUNDS AND METHODS
  [FR] COMPOSÉS ET MÉTHODES THÉRAPEUTIQUES

  摘要：

  本文披露了以下式I的化合物：(I)或其药学上可接受的盐，其中R1、R2和R3可以是本文中定义的任何值，以及包含这种化合物的组合物。还披露了治疗疾病的方法，包括神经退行性疾病，如帕金森病和阿尔茨海默病。

  公开号：

  WO2020010021A1
• 作为产物：
  描述：

  (S)-3-Benzylamino-2-tert-butoxycarbonylamino-propionic acid 在 1,4-环己二烯 、 palladium 10% on activated carbon 作用下， 以 乙醇 为溶剂， 生成 (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid
  参考文献：
  名称：

  从 d-丝氨酸获得的 2,3-二氨基丙醇作为合成受保护的 2,3-l-二氨基丙酸 (l-Dap) 甲酯的中间体

  摘要：

  开发了一种用于制备非蛋白氨基酸 2,3-l-二氨基丙酸 (l-Dap) 的两个正交保护甲酯的合成策略。在这些结构中，碱不稳定保护基团 9-芴基甲氧羰基 (Fmoc) 与对甲苯磺酰基 (tosyl, Ts) 或酸不稳定的叔丁氧羰基 (Boc) 部分配对。受保护的 l-Dap 甲酯的合成方法使用适当掩蔽的 2,3-二氨基丙醇，这是通过对由商业氨基酸 Nα-Fmoc-O-叔丁基-d-丝氨酸制备的醛进行还原胺化获得的，用作起始材料。还原胺化是用伯胺和磺酰胺进行的，该过程由路易斯酸 Ti(OiPr)4 辅助。通过氧化2的醇官能团来安装所需的羧基，在 3-NH2 位点带有甲苯磺酰基或苄基保护基团的 3-二氨基丙醇。使用每个步骤后获得的粗产物可以轻松应用该程序，最大限度地减少色谱纯化的需要。起始 d-丝氨酸模板的碳原子手性在所有合成步骤中均保持不变。

  DOI：

  10.3390/molecules25061313

文献信息

• [EN] ANTIBODY DRUG CONJUGATES<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2020229982A1

  公开（公告）日：2020-11-19

  The present disclosure provides antibody drug conjugates comprising STING modulators. Also provided are compositions comprising the antibody drug conjugates. The compounds and compositions are useful for stimulating an immune response in a subject in need thereof. Formula (I):

  本公开提供包含STING调节剂的抗体药物结合物。还提供了包含该抗体药物结合物的组合物。这些化合物和组合物对于刺激需要免疫反应的受试者是有用的。公式（I）:
• Synthesis and Biological Activity of (S)-2-Amino-3(2,5-dihydro-5-oxo-4-isoxazolyl)propanoic Acid (TAN-950 A) Derivatives.
  作者：Norikazu TAMURA、Yoshihiro MATSUSHITA、Toshi IWAMA、Setsuo HARADA、Shoji KISHIMOTO、Katsumi ITOH

  DOI：10.1248/cpb.39.1199

  日期：——

  starting with methyl (S)- and (R)-N-Boc-pyroglutamate (8) via acylation at the C-4 position followed by isoxazolone formation with hydroxylamine and subsequent deprotection reactions. The lactam 16, prepared from (RS)-aminoadipic acid, and dimethyl esters 19 of (R)- and (S)-aspartic acid were converted to (RS)-3-methyl-homo-TAN-950 A (15i) and optically active nor-TAN-950 A derivatives 15j--o, respectively

  （S）-2-氨基-3-（2,5-二氢-5-氧代-4-异恶唑基）丙酸（TAN-950 A（1））是一种新型氨基酸抗生素，对谷氨酸受体具有高亲和力中枢神经系统。为了提高对谷氨酸受体的亲和力，研究了TAN-950 A衍生物6a-o，15a-o的构效关系。以（S）-和（R）-N-Boc-焦谷氨酸甲酯（8）为起始原料，通过C-4位的酰化反应合成旋光性TAN-950 A类似物15a-h，然后与羟胺形成异恶唑酮并随后脱保护反应。将由（RS）-氨基己二酸和（R）-和（S）-天冬氨酸的二甲酯19制备的内酰胺16转化为（RS）-3-甲基-homo-TAN-950 A（15i）和利用相似的反应序列分别对光学活性的nor-TAN-950 A衍生物15j-o进行了研究。大多数TAN-950 A衍生物6a-o，15a-o对谷氨酸受体具有亲和力。3-烷基衍生物15b，d-g特别显示出对喹喹啉亚型受体的高亲和力，并对海马
• Proteasome inhibitors and methods of using the same
  申请人：Bernardini Raffaella

  公开号：US20060189806A1

  公开（公告）日：2006-08-24

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly or indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以调节细胞凋亡，例如通过抑制蛋白酶体活性。这些化合物和组合物可用于诱导细胞凋亡和治疗癌症等疾病，以及与蛋白酶体活性直接或间接相关的其他疾病。
• [EN] TETRAHYDRO-BENZODIAZEPINONES<br/>[FR] TÉTRAHYDRO-BENZODIAZÉPINONES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015071393A1

  公开（公告）日：2015-05-21

  Disclosed are compounds of Formula I, or pharmaceutically acceptable salts thereof, wherein W, X, Y, Z, R1, R2, R3, R4 and R5 are as described in this application, and methods of using said compounds in the treatment of cancer.

  本申请公开了具有I式化合物或其药用可接受盐的化合物，其中W、X、Y、Z、R1、R2、R3、R4和R5如本申请所述，并且使用所述化合物治疗癌症的方法。
• [EN] MODULATORS OF CELLULAR ADHESION<br/>[FR] MODULATEURS DE L'ADHESION CELLULAIRE
  申请人：SUNESIS PHARMACEUTICALS INC

  公开号：WO2005044817A1

  公开（公告）日：2005-05-19

  The present invention provides compounds having formula (I): and pharmaceutically acceptable derivatives thereof, wherein R1-R4, n, p, A, B, D, E, L and AR1 are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders mediated by the CD11/CD18 family of cellular adhesion molecules (e.g., LFA-1).

  本发明提供具有以下式（I）的化合物及其药学上可接受的衍生物，其中R1-R4、n、p、A、B、D、E、L和AR1如本文中一般描述的那样，并且另外提供这些药物组合物以及用于治疗由CD11/CD18细胞粘附分子家族介导的疾病（例如LFA-1）的使用方法。