O-苄基-L-丝氨酸甲酯盐酸盐 | 19525-87-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丝氨酸类衍生物
• 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: O-苄基-L-丝氨酸甲酯盐酸盐
• 中文别名: 甲基-O-苄基-L-丝氨酸酯盐酸盐；O-苯甲基-L-丝胺酸甲基酯盐酸盐；(S)-2-氨基-3-(苄氧基)丙酸甲酯盐酸盐
• 英文名称: O-methyl O-benzyl-L-serinate hydrochloride
• 英文别名: O-benzyl-L-serine methyl ester hydrochloride；(S)-Methyl 2-amino-3-(benzyloxy)propanoate hydrochloride；methyl (2S)-2-amino-3-phenylmethoxypropanoate;hydrochloride
• CAS: 19525-87-2
• 化学式: C₁₁H₁₅NO₃*ClH
• 分子量: 245.706
• InChiKey: UDHSAWHYRXHQJP-PPHPATTJSA-N

物化性质

• 熔点：
  164-166 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2923900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储温度应保持在0°C。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: O-Benzyl-l-serine methyl ester, HCl
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: O-Benzyl-l-serine methyl ester, HCl
CAS number: 19525-87-2

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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: C11H15NO3.ClH
Molecular weight: 245.7

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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, hydrogen chloride.

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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

H-Ser(Bzl)操作手册。HCl是一种丝氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  O-苄基-L-丝氨酸甲酯盐酸盐 在 锂硼氢 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol
  参考文献：
  名称：

  Convenient Procedures for the Synthesis of N-BOC-D-Serinal Acetonide from L-Serine

  摘要：

  本文介绍了从天然 L-丝氨酸开始制备对映体纯度为 N-BOC-D-丝氨酸丙酮（加纳醛的对映体）的两条直接合成路线。

  DOI：

  10.1055/s-1997-3186
• 作为产物：
  描述：

  O-benzyl-L-serine methyl ester 在 甲醇 、 乙酰氯 作用下， 生成 O-苄基-L-丝氨酸甲酯盐酸盐
  参考文献：
  名称：

  Continuous Multiple Liquid–Liquid Separation: Diazotization of Amino Acids in Flow

  摘要：

  A second-generation laboratory-scale, modular liquid-liquid separation device based on computer-controlled high-pressure pumps and a high. resolution digital camera has been invented. The diazotization of amino acids to produce valuable chiral hydroxyacids is demonstrated in flow for the first time. The use of a triple-separator system in conjuction with the developed diazotization process allows the safe and efficient production and automated isolation of multigram quantities of valuable chiral hydroxyacids.

  DOI：

  10.1021/ol301930h

文献信息

• Efficient synthesis of 2,5-diketopiperazines using microwave assisted heating
  作者：Marcus Tullberg、Morten Grøtli、Kristina Luthman

  DOI：10.1016/j.tet.2006.05.010

  日期：2006.7

  In this study a general, efficient and environmentally benign solution phase synthesis of 2,5-diketopiperazines (DKPs) using microwave assisted heating in water is described. A series of 11 structurally different DKPs have been synthesized from dipeptide methyl esters. A range of common laboratory solvents have been tested as well as different reaction times and temperatures. Both classic thermal and

  在这项研究中，描述了使用水中微波辅助加热的2，5-二酮哌嗪（DKP）的一般，有效和环境友好的溶液相合成方法。由二肽甲酯合成了一系列11种结构不同的DKP。已测试了一系列常见的实验室溶剂以及不同的反应时间和温度。经典的加热和微波辅助加热均已进行了研究。到目前为止，以水为溶剂的微波辅助加热10分钟被证明是最有效的环化方法，可产生中等至极佳的DKP收率（63-97％）。与其他已公开的程序相反，此方法似乎与氨基酸序列无关。
• A General Approach to the Aza-Diketomorpholine Scaffold
  作者：Mathéo Berthet、Baptiste Legrand、Jean Martinez、Isabelle Parrot

  DOI：10.1021/acs.orglett.6b03656

  日期：2017.2.3

  A stereoconservative three-step synthesis to access to 1,2,4-oxadiazine-3,6-dione is presented. This underexplored platform could be considered as a constrained oxy-azapeptide or an aza-diketomorpholine, the methodology being then successfully applied to produce enantiopure aza-analogs of diketomorpholine natural products. Importantly, the first crystal structures were obtained and compared to diketomorpholine

  提出了一种立体保守的三步合成法，以合成1,2,4-恶二嗪-3,6-二酮。该未充分开发的平台可以被认为是受约束的氧-氮杂肽或氮杂-二酮吗啉，该方法随后成功地用于生产对映纯的二酮吗啉天然产物的氮杂类似物。重要的是，获得了第一晶体结构并将其与二酮吗啉和二酮哌嗪结构进行比较。最后，描述了有关该杂环支架与各种氨基酸的偶联以提供原始假二肽类似物的简单方法。
• Amino Acid Conjugates of Lithocholic Acid As Antagonists of the EphA2 Receptor
  作者：Matteo Incerti、Massimiliano Tognolini、Simonetta Russo、Daniele Pala、Carmine Giorgio、Iftiin Hassan-Mohamed、Roberta Noberini、Elena B. Pasquale、Paola Vicini、Silvia Piersanti、Silvia Rivara、Elisabetta Barocelli、Marco Mor、Alessio Lodola

  DOI：10.1021/jm301890k

  日期：2013.4.11

  Structure–activity relationships indicate that the presence of a lipophilic amino acid side chain is fundamental to achieve good potencies. The l-Trp derivative (20, PCM126) was the most potent antagonist of the series disrupting EphA2–ephrinA1 interaction and blocking EphA2 phosphorylation in prostate cancer cells at low μM concentrations, thus being significantly more potent than LCA. Compound 20 is among

  Eph 受体-ephrin 系统是开发新型抗血管生成药物的新兴目标。我们最近发现石胆酸 (LCA) 是一种能够阻断癌细胞中依赖 EphA2 信号的小分子，这表明其 (5β)-cholan-24-oic 酸支架可用作模板来设计新一代改进的EphA2 拮抗剂。在这里，我们报告了通过将其羧基与不同的 α-氨基酸共轭而获得的一组扩展 LCA 衍生物的设计和合成。构效关系表明亲脂性氨基酸侧链的存在是实现良好效力的基础。的升-Trp衍生物（20, PCM126) 是该系列中最有效的拮抗剂，可在低 μM 浓度下破坏 EphA2-ephrinA1 相互作用并阻断前列腺癌细胞中的 EphA2 磷酸化，因此比 LCA 更有效。化合物20是 EphA2 受体最有效的小分子拮抗剂之一。
• [EN] SUBSTITUTED AMINO-BENZIMIDAZOLES, MEDICAMENTS COMPRISING SAID COMPOUND, THEIR USE AND THEIR METHOD OF MANUFACTURE<br/>[FR] AMINO-BENZIMIDAZOLES SUBSTITUÉS, MÉDICAMENTS COMPRENANT LEDIT COMPOSÉ, LEUR UTILISATION ET LEUR PROCÉDÉ DE FABRICATION
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009092566A1

  公开（公告）日：2009-07-30

  The present invention relates to substituted amino-benzimidazoles of general formula (1) wherein the groups R1 to R14 and A, are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.

  本发明涉及一般式（1）中的取代氨基苯并咪唑，其中基团R1至R14和A如规范和索赔中定义，并其用于治疗阿尔茨海默病（AD）和类似疾病。
• NOVEL SMALL MOLECULE DNAK INHIBITORS
  申请人：Sturgess Michael Alan

  公开号：US20100087466A1

  公开（公告）日：2010-04-08

  Methods of inhibiting HSP70 proteins, agents causing the inhibition of HSP70 proteins, and the effects of such inhibition on cell proliferation. Anti-microbial agents comprising small molecules, or pharmaceutical salts thereof, disclosed herein and further methods of use thereof are also disclosed. The disclosed small molecules, or pharmaceutical salts thereof, are effective in inhibiting microbial chaperone activity in microbes, such as homologs of HSP70. The disclosed small molecules, or pharmaceutical salts thereof, are also effective for the therapeutic treatment of cancer.

  抑制HSP70蛋白的方法，导致抑制HSP70蛋白的药剂，以及这种抑制对细胞增殖的影响。本文还披露了包含小分子或其药用盐的抗微生物药剂，以及其进一步的使用方法。所披露的小分子或其药用盐对微生物中的分子伴侣活性具有抑制作用，例如HSP70同源物。所披露的小分子或其药用盐还对癌症的治疗治疗有效。