L-丝氨酸叔丁酯盐酸盐 | 106402-41-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 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: L-丝氨酸叔丁酯盐酸盐
• 中文别名: L-丝氨酸-叔丁酯盐酸盐；丝氨酸叔丁酯盐酸盐；苯胺,3-[4-(苯基甲基)苯氧基]-；H-Ser-OtBu・HCl
• 英文名称: L-serine tert-butyl ester hydrochloride
• 英文别名: tert-butyl L-serinate hydrochloride；serine tert butyl ester hydrochloride；H-Ser-O-tBu hydrochloride；(S)-tert-Butyl 2-amino-3-hydroxypropanoate hydrochloride；tert-butyl (2S)-2-amino-3-hydroxypropanoate;hydrochloride
• CAS: 106402-41-9
• 化学式: C₇H₁₅NO₃*ClH
• 分子量: 197.662
• InChiKey: TUDHOGYHZNNYHW-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  72.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温和干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Ser-otbu 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: H-Ser-otbu hcl
CAS number: 106402-41-9

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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: C7H15NO3.ClH
Molecular weight: 197.7

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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

用途

丝氨酸叔丁酯盐酸盐主要用于合成2型糖尿病抑制剂，同时也用于合成双功能和三功能螯合剂。

反应信息

• 作为反应物：
  描述：

  L-丝氨酸叔丁酯盐酸盐 在 三乙胺 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.03h， 生成 4-benzyl-2-phenyl-1,3-oxazoline-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  An unusual base-dependent α-alkylation and β-elimination of tert-butyl 2-phenyl-2-oxazoline-4-carboxylate: practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate

  摘要：

  Practical synthesis of (+/-)-alpha-alkylserines and tert-butyl benzamidoacrylate from tert-butyl 2-phenyl-2-oxazoline-4-carboxylate (6) were developed. The alpha-alkylation and beta-elimination of 6 are dramatically dependent upon base conditions. The phase-transfer catalytic condition bearing solid KOH in toluene gives alpha-alkylation (up to >99%), and t-BuOK in DMF gives beta-elimination (98%). (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.03.041
• 作为产物：
  描述：

  N-叔丁氧羰基丝氨酸叔丁酯 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 L-丝氨酸叔丁酯盐酸盐
  参考文献：
  名称：

  Selective Removal of an N-BOC Protecting Group in the Presence of a tert-Butyl Ester and Other Acid-Sensitive Groups

  摘要：

  DOI：

  10.1021/jo00090a045

文献信息

• Design, synthesis, evaluation, and SAR of 4-phenylindoline derivatives, a novel class of small-molecule inhibitors of the programmed cell death-1/ programmed cell death-ligand 1 (PD-1/PD-L1) interaction
  作者：Yang Yang、Ke Wang、Hao Chen、Zhiqiang Feng

  DOI：10.1016/j.ejmech.2020.113001

  日期：2021.2

  blockade of the PD-1/PD-L1 immune checkpoint pathway with small molecules is an emerging immunotherapeutic approach. A novel series of 4-phenylindoline derivatives were synthesized, and their inhibitory activity against the PD-1/PD-L1 protein-protein interaction (PPI) was evaluated through a homogenous time-resolved fluorescence (HTRF) assay. Among them, A20 and A22 exhibited potent activity with IC50

  用小分子阻断PD-1 / PD-L1免疫检查点途径是一种新兴的免疫治疗方法。合成了一系列新的4-苯基二氢吲哚衍生物，并通过均相时间分辨荧光（HTRF）分析评估了它们对PD-1 / PD-L1蛋白质-蛋白质相互作用（PPI）的抑制活性。其中，A20和A22表现出有效的活性，IC 50值分别为17 nM和12 nM。此外，A20对与EC 50相互作用的PD-1 / PD-L1具有抑制作用在表达PD-L1 / TCR激活因子的CHO细胞和表达PD-1的Jurkat细胞的共培养模型中，聚合酶链反应的0.43μM值 此外，总结了新型合成的4-苯基二氢吲哚衍生物的构效关系（SAR），并通过分子模拟和对接分析了A22与PD-L1二聚体的结合方式，证明了N原子在侧面二氢吲哚片段的链可与PD-L1蛋白的氨基酸残基相互作用，从而导致有效的抑制活性。这项研究为进一步的药物设计提供了新的见识。
• [EN] DIPHENYLAZETIDINONE DERIVATES POSSESSING CHOLESTEROL ABSORPTION INHIBITORY ACTIVITY<br/>[FR] DERIVES DIPHENYLAZETIDINONE A ACTIVITE INHIBITRICE DE L'ABSORPTION DU CHOLESTEROL
  申请人：ASTRAZENECA AB

  公开号：WO2005061452A1

  公开（公告）日：2005-07-07

  Compounds of formula (I) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.

  化合物的结构式（其中变量基团如定义所示）及其药学上可接受的盐、溶剂合物、该类盐的溶剂合物和它们的前药，以及它们作为治疗高脂血症的胆固醇吸收抑制剂的用途被描述。还描述了它们的制备方法和含有它们的药物组合物。
• Discovery of a Highly Potent, Nonabsorbable Apical Sodium-Dependent Bile Acid Transporter Inhibitor (GSK2330672) for Treatment of Type 2 Diabetes
  作者：Yulin Wu、Christopher J. Aquino、David J. Cowan、Don L. Anderson、Jeff L. Ambroso、Michael J. Bishop、Eric E. Boros、Lihong Chen、Alan Cunningham、Robert L. Dobbins、Paul L. Feldman、Lindsey T. Harston、Istvan W. Kaldor、Ryan Klein、Xi Liang、Maggie S. McIntyre、Christine L. Merrill、Kristin M. Patterson、Judith S. Prescott、John S. Ray、Shane G. Roller、Xiaozhou Yao、Andrew Young、Josephine Yuen、Jon L. Collins

  DOI：10.1021/jm400459m

  日期：2013.6.27

  of ASBT inhibitors for treatment of type 2 diabetes has been relatively unexplored. We initiated a lead optimization effort that focused on the identification of a potent, nonabsorbable ASBT inhibitor starting from the first-generation inhibitor 264W94 (1). Extensive SAR studies culminated in the discovery of GSK2330672 (56) as a highly potent, nonabsorbable ASBT inhibitor which lowers glucose in an

  根尖钠依赖性胆汁酸转运蛋白（ASBT）通过门静脉将胆汁盐从胃肠道（GI）的管腔转运到肝脏。多家制药公司已经开发出ASBT与肝胆固醇代谢之间的生理联系，从而开展了ASBT抑制剂作为降血脂药的临床研究。尽管显示出适度的脂质作用，但相对未开发ASBT抑制剂治疗2型糖尿病的潜在效用。我们启动了一项领先的优化工作，重点是从第一代抑制剂264W94（1）开始鉴定有效的，不可吸收的ASBT抑制剂。广泛的SAR研究最终发现了GSK2330672（56）是一种高效，不可吸收的ASBT抑制剂，可降低2型糖尿病动物模型中的葡萄糖并显示出极好的可开发性，可用于评估不可吸收的ASBT抑制剂在治疗2型糖尿病患者中的潜在治疗作用。
• TRIAZOLE-ISOXAZOLE COMPOUND AND MEDICAL USE THEREOF
  申请人：JAPAN TOBACCO INC.

  公开号：US20160137639A1

  公开（公告）日：2016-05-19

  A compound represented by Formula [I]: or pharmaceutically acceptable salt thereof, wherein each symbol is as defined in the description.

  由式[I]表示的化合物： 或其药学上可接受的盐，其中每个符号如描述中所定义。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011137135A1

  公开（公告）日：2011-11-03

  Compounds of Formula (I) and methods for treating metabolic disorders are disclosed.

  公开了化合物的公式（I）以及治疗代谢性疾病的方法。