2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester | 95715-85-8

• 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
• 英文名称: 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester
• 英文别名: methyl (tert-butoxycarbonyl)-D-serinate；(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate；N-(tert-butoxycarbonyl)-D-serine methyl ester；Boc-D-Ser-OMe；N-Boc D-serine methyl ester；methyl (2R)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate；N-[(1,1-Dimethylethoxy)carbonyl]-D-serine methyl ester；(R)-N-Boc-serine methyl ester；Boc-D-serine methyl ester；N-Boc-D-Ser-OMe；methyl (R)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate；methyl N-(tert-butoxycarbonyl)-D-serinate；methyl 3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 95715-85-8
• 化学式: C₉H₁₇NO₅
• mdl: MFCD03756651
• 分子量: 219.238
• InChiKey: SANNKFASHWONFD-UHFFFAOYSA-N

物化性质

• 沸点：
  215 °C(lit.)
• 密度：
  1.08 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 溶解度：
  可溶于氯仿、甲醇
• 稳定性/保质期：
  避免接触强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2924199090
• 危险品运输编号：
  NONH for all modes of transport
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。储存时，请确保放置在阴凉、干燥处。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : N-(tert-Butoxycarbonyl)-D-serine methyl ester
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 95715-85-8
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C9H17NO5
Molecular Weight : 219,23 g/mol
CAS-No. : 95715-85-8
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. Use respirators and components tested and approved under
appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 215 °C - lit.
boiling range
g) Flash point 113 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 1,08 g/mL at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

BOC-D-丝氨酸甲酯

BOC-D-丝氨酸甲酯是合成嘌呤、胸腺嘧啶和胆碱的重要前体，适用于实验室生物合成过程。

合成方法

步骤1： 将78.4克（0.359摩尔）的(BOC)2O溶解在二恶烷中（总体积280毫升），然后在0.5小时内缓慢加入到31.73克（0.3019摩尔）D-丝氨酸的1 N NaOH溶液（620毫升）冰冷的混合液中。随后将该溶液升温至室温，并搅拌3.5小时。通过(TLC)薄层层析法检测，产物形成清晰，Rf值为0.65，同时牺牲了部分起始氨基酸。之后，在35℃下旋转蒸发浓缩混合物至初始体积的一半，然后在冰浴中冷却，通过缓慢加入冷的1 N KHSO4溶液（620毫升）调节pH至2-3，并用乙酸乙酯进行三次萃取（每次1000毫升）。合并后的有机相经过MgSO4干燥、过滤及真空浓缩，最终得到无色粘性泡沫状N-BOC D-丝氨酸2b。

步骤2： 将所得的N-BOC D-丝氨酸2b溶解在600毫升乙醚中，并在冰浴中冷却。随后以10个50毫升批次添加冷的0.6 M醚重氮甲烷溶液，总共30分钟后在0℃下搅拌。通过(TLC)薄层层析法验证酯形成清晰，Rf值为0.38，同时牺牲了起始原料。过量的重氮甲烷用乙酸破坏，所得混合物再用半饱和NaHCO3溶液（300毫升）和盐水（200毫升）分别萃取，再经MgSO4干燥、过滤及真空浓缩处理后，得到无色粘性泡沫状N-BOC甲酯3b。直接获得的产物无需进一步纯化即可作为BOC-D-丝氨酸甲酯使用。测得其比旋光度为[α]20D = -10.2°（在CHCl3中的浓度c＝1.02），[α]20D = -5.9°（在CHCl3中的浓度c＝2.61）。

反应信息

• 作为反应物：
  描述：

  2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 对甲苯磺酰氯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以94%的产率得到2-叔丁氧羰基氨基丙烯酸甲酯
  参考文献：
  名称：

  从 DL-丝氨酸和苏氨酸轻松获得 α,β-脱氢丙氨酸和 α,β-脱氢氨基丁酸衍生物

  摘要：

  摘要 α,β-脱氢氨基酸不仅是自然界中许多生物活性肽的重要组成部分，而且还是有机合成中各种合成氨基酸的重要组成部分。文献中广泛报道了制备脱氢氨基酸的方法；然而，仍然需要有效和方便的协议。在这里，我们开发了一种方便的方法来制备分别衍生自 DL-丝氨酸和 DL-苏氨酸的脱氢丙氨酸 (ΔAla) 和脱氢氨基丁酸 (ΔAbu) 衍生物。该工艺采用4-甲苯磺酰氯(TsCl)和1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)，一锅完成羟基的活化和β-消除。由于方便易行，这种方法会引起合成化学家的注意。

  DOI：

  10.1080/00397911.2016.1149194
• 作为产物：
  描述：

  2-(叔丁氧羰基氧亚氨基)-2-苯乙腈 在 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 生成 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester
  参考文献：
  名称：

  类胡萝卜素的无环类似物的合成和神经兴奋活性

  摘要：

  合成了4-苄基谷氨酸的四种构型异构体，即类胡萝卜素的无环类似物，以检验它们的构效关系。

  DOI：

  10.1016/s0040-4039(01)80659-6

文献信息

• Total Synthesis of TMC-95A and -B via a New Reaction Leading to <i>Z</i>-Enamides. Some Preliminary Findings as to SAR
  作者：Songnian Lin、Zhi-Qiang Yang、Benjamin H. B. Kwok、Michael Koldobskiy、Craig M. Crews、Samuel J. Danishefsky

  DOI：10.1021/ja049821k

  日期：2004.5.1

  A full account of the total syntheses of proteasome inhibitors TMC-95A and -B is provided. A key feature of the syntheses involved installation of a cis-propenylamide moiety by a thermal rearrangement of an alpha-silylallyl amide. The scope and mechanism of the enamide-forming reaction are discussed. Also provided are some preliminary results from SAR studies. It was found that simplified analogues

  提供了蛋白酶体抑制剂 TMC-95A 和 -B 的全合成的完整说明。合成的一个关键特征涉及通过α-甲硅烷基烯丙基酰胺的热重排安装顺式丙烯酰胺部分。讨论了烯酰胺形成反应的范围和机理。还提供了一些 SAR 研究的初步结果。发现简化的类似物可以保留蛋白酶体抑制的全部效力。
• 作为细胞坏死阻碍剂的吲哚化合物
  申请人：株式会社LG化学

  公开号：CN105636956B

  公开（公告）日：2019-07-09

  本发明涉及化学式(1)的吲哚化合物、或者其药学容许的盐或异构体，及以含有此作为活性成分作为特征的用于预防或治疗细胞坏死及其关联疾病的组合物及组合物的制造方法。
• [EN] BIARYL KINASE INHIBITORS<br/>[FR] INHIBITEURS BIARYLES DE KINASES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2017059080A1

  公开（公告）日：2017-04-06

  The present disclosure is directed to biaryl compounds of formula (I) which can inhibit AAKl (adaptor associated kinase 1), compositions comprising such compounds and their use for treating e.g. pain, Alzheimer's disease, Parkinson's disease and schizophrenia.

  本公开涉及公式（I）的联苯化合物，可以抑制AAK1（适配器相关激酶1），包括这种化合物的组合物以及它们用于治疗疼痛、阿尔茨海默病、帕金森病和精神分裂症等的用途。
• Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis
  作者：Tomer M. Faraggi、Caroline Rouget-Virbel、Juan A. Rincón、Mario Barberis、Carlos Mateos、Susana García-Cerrada、Javier Agejas、Oscar de Frutos、David W. C. MacMillan

  DOI：10.1021/acs.oprd.1c00208

  日期：2021.8.20

  wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds

  我们在本文中描述了将丝氨酸转化为多种光学纯非天然氨基酸的两步过程。该方法利用溴代烷基中间体和多种芳基卤化物之间的光催化交叉亲电偶联来生产苯丙氨酸、色氨酸和组氨酸的人工类似物。该反应具有广泛的功能，可用于通过流动技术可扩展地合成有价值的药物支架。
• [EN] COMBINATION OF HEPATITIS B VIRUS (HBV) VACCINES AND PYRIDOPYRIMIDINE DERIVATIVES<br/>[FR] ASSOCIATION DE VACCINS CONTRE LE VIRUS DE L'HÉPATITE B (VHB) ET DE DÉRIVÉS DE PYRIDOPYRIMIDINE
  申请人：JANSSEN SCIENCES IRELAND UNLIMITED CO

  公开号：WO2020255038A1

  公开（公告）日：2020-12-24

  Therapeutic combinations of hepatitis B virus (HBV) vaccines and a pyridopyrimidine derivative are described. Methods of inducing an immune response against HBV or treating an HBV-induced disease, particularly in individuals having chronic HBV infection, using the disclosed therapeutic combinations are also described. The invention provides therapeutic combinations or compositions and methods for inducing an immune response against hepatitis B viruses (HBV) infection.

  本发明描述了乙型肝炎病毒（HBV）疫苗和吡啶吡嘧啶衍生物的治疗组合。还描述了利用所述治疗组合诱导免疫应答对抗HBV或治疗HBV引起的疾病的方法，特别是在患有慢性HBV感染的个体中。该发明提供了用于诱导免疫应答对抗乙型肝炎病毒（HBV）感染的治疗组合或组成物和方法。