N-叔丁氧羰基丝氨酸叔丁酯 | 7738-22-9

• 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: N-叔丁氧羰基丝氨酸叔丁酯
• 中文别名: N-BOC-L-丝氨酸叔丁酯
• 英文名称: N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester
• 英文别名: tert-butyl (tert-butoxycarbonyl)-L-serinate；Boc-Ser(OtBu)；Boc-L-Ser-Ot-Bu；Boc-L-Serine tert-butyl ester；N-Boc-L-serine tert butyl ester；tert-butyl (2S)-2-[(tert-butoxy)carbonyl]amino-3-hydroxypropanoate；tert-butyl 2-(S)-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate；N-tert-butoxycarbonyl-L-serine tert-butyl ester；tert-butoxycarbonyl-L-serine tert-butyl ester；N-Boc-Ser-OtBu；Boc-Ser-Otbu；tert-butyl (2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 7738-22-9
• 化学式: C₁₂H₂₃NO₅
• 分子量: 261.318
• InChiKey: NSNZHQVMWJPBPI-QMMMGPOBSA-N

物化性质

• 熔点：
  80℃
• 沸点：
  381.9±32.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，干燥密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-ser-otbu
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: Boc-ser-otbu
CAS number: 7738-22-9

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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: C12H23NO5
Molecular weight: 261.3

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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

制备方法与用途

Boc-Ser-OtBu是一种丝氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基丝氨酸叔丁酯 在 palladium on activated charcoal sodium azide 、 四丁基溴化铵 、 氢气 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 tert-butyl (2S)-3-amino-2-(tert-butoxycarbonylamino)propanoate
  参考文献：
  名称：

  Deamido Bleomycin A2 的全合成，抗肿瘤剂博来霉素的主要分解物

  摘要：

  抗肿瘤抗生素博来霉素的代谢失活被认为仅通过博来霉素水解酶的作用介导，博来霉素水解酶是一种在自然界中广泛分布的半胱氨酸蛋白酶。虽然博来霉素表现出的抗肿瘤活性谱被认为反映了博来霉素水解酶在宿主体内的解剖分布，但很少有人在化学或生化水平上表征推定失活的产物。本报告描述了 deamidobleomycin demethyl A(2) (3) 和 deamido bleomycin A(2) (4) 的合成，以及各自的苷元。这些化合物都可以通过关键中间体 N(alpha)-Boc-N(beta)-[1-amino-3(S)-(4-amino-6-carboxy-5-methylpyrimidin-2-yl)propion- 3-基]-(S)-β-氨基丙氨酸叔丁酯(16)。合成 deamido 博来霉素 A(2) 显示与博来霉素 A(2) 与人博来霉素水解酶处理形成的产品相同，如反相 HPLC 分析和

  DOI：

  10.1021/ja012741l
• 作为产物：
  描述：

  N-BOC-O-苄基-L-丝氨酸 在 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 5.08h， 生成 N-叔丁氧羰基丝氨酸叔丁酯
  参考文献：
  名称：

  手性环状氨基磺酸酯前体的开环亲核11C氰化反应合成l [[4-11C]天冬酰胺

  摘要：

  合成方便的，快速的方法以合成放射性标记的，对映体纯的氨基酸（AAs）作为潜在的正电子发射断层扫描（PET）成像剂，以绘制活体生物的各种生化转变仍然是一个挑战。鉴于碳11的半衰期较短（11 C，t 1/2 = 20.4分钟），对于碳11标记的AA的合成尤其如此。制备对映体纯的11 C标记的l的简便合成途径用部分保护的丝氨酸为原料开发了天冬酰胺，并进行了四步转化，提供了手性五元环氨基磺酸盐作为放射性标记前体。X射线晶体学证实了其结构和绝对构型。利用[ 11 C]的氰化物亲核开环反应，接着通过选择性酸性水解和脱保护，对映体纯升- [4- 11 C]天冬酰胺的合成。反应参数的进一步优化，包括碱金属离子源，溶剂，酸成分，反应温度和反应时间，用于合成可靠两步法升- [4- 11 C]天冬酰胺被提出：45±3分钟内（n从轰击结束= 5，合成了所需的对映体纯产物，其初始亲核氰化产率为69±4％（n = 5），两步放射化学总产率为53±2％（n

  DOI：

  10.1002/chem.201801029

文献信息

• Selective nitrolytic deprotection of N -BOC-amines and N -BOC-amino acids derivatives
  作者：Paolo Strazzolini、Tiziana Melloni、Angelo G Giumanini

  DOI：10.1016/s0040-4020(01)00900-0

  日期：2001.10

  configuration of the substrates and without affecting copresent Z and ester functions, with a remarkable selectivity towards acid sensitive t-butyl esters. The obtained amino acids esters, isolated and characterized in the form of nitrates salts, proved to be suitable intermediates to be used in peptide synthesis.

  使用HNO去保护的方法的延伸3在CH 2氯2到多个适当选择的Ñ -BOC-掩蔽胺和天然氨基酸的衍生物进行了研究。发现该方法对几乎所有测试的底物均有效，但活化的芳族胺和杂环不可避免地会经历更快的氧化。丙氨酸，苯丙氨酸，丝氨酸和赖氨酸衍生物以及二肽Ala–Phe被有效地脱保护，保留了底物的构型且不影响共存的Z和酯功能，对酸敏感的t具有显着的选择性。丁酯。分离出并以硝酸盐的形式表征的所得氨基酸酯被证明是适用于肽合成的中间体。
• <i>N</i>-Heterocyclic Carbene Catalyzed Stereoselective Glycosylation of 2-Nitrogalactals
  作者：Jia-Lin Liu、Yu-Tong Zhang、Hang-Fan Liu、Ling Zhou、Jie Chen

  DOI：10.1021/acs.orglett.7b02543

  日期：2017.10.6

  An efficient N-heterocyclic carbene catalyzed glycosylation of 2-nitrogalactals with alcohols and phenol has been developed for the first time. A wide variety of 1,2-cis-2-nitroglycosides can be obtained with good to excellent yields and high to excellent α-selectivities.

  首次开发了一种有效的N-杂环卡宾催化2-硝基半乳糖与醇和苯酚的糖基化反应。可以以高至优异的产率和高至优异的α-选择性获得各种各样的1,2-顺式-2-硝基糖苷。
• Late-stage peptide and protein modifications through phospha-Michael addition reaction
  作者：Pei-Yang He、Huai Chen、Hong-Guo Hu、Jin-Jian Hu、Yeh-Jun Lim、Yan-Mei Li

  DOI：10.1039/d0cc04969g

  日期：——

  We developed a late-stage modification strategy by a phospha-Michael addition reaction between various functional phosphines and unprotected dehydroalanine (Dha) peptides and proteins under mild conditions. This strategy was applied to generate a staple peptide to enhance its cell membrane penetrability, and it was also able to regulate α-synuclein aggregation properties and morphological characteristics

  我们通过在温和条件下各种功能性膦与未保护的脱氢丙氨酸（Dha）肽和蛋白质之间的磷-迈克尔加成反应开发了后期修饰策略。该策略被用于产生主要肽以增强其细胞膜的穿透性，并且还能够通过添加不同的电荷来调节α-突触核蛋白的聚集性质和形态特征。
• Chemoselective hydrolysis of tert-butyl esters in acetonitrile using molecular iodine as a mild and efficient catalyst
  作者：J.S. Yadav、E. Balanarsaiah、S. Raghavendra、M. Satyanarayana

  DOI：10.1016/j.tetlet.2006.05.011

  日期：2006.7

  A simple, mild and efficient method for the hydrolysis of tert-butyl esters using molecular iodine as a catalyst is described. Acid labile protecting groups, such as N-Boc, OBn, OAc and double bonds, are compatible under the reaction conditions.

  描述了一种使用分子碘作为催化剂水解叔丁酯的简单，温和有效的方法。酸不稳定的保护基团，例如N -Boc，OBn，OAc和双键在反应条件下是相容的。
• Compound comprising a fluorine-substituted alkyl group and a liposome contrast medium comprising the compound
  申请人：FUJIFILM Corporation

  公开号：EP1916255A3

  公开（公告）日：2012-08-22

  A steroid ester compound of a terminally-fluorinated alkyl fatty acid, a steroid compound having bis(trifluoromethyl)phenyl group, a phosphatidylserine compound having a terminally-fluorinated alkyl group, a glyceride compound having bis(trifluoromethyl phenyl group, or a glyceride compound having a terminally-fluorinated alkyl group. A vascular lesion can be selectively imaged by using a contrast medium comprising a liposome containing said compound or a salt thereof.

  一种具有终端氟化烷基脂肪酸的类固醇酯化合物，一种具有双(三氟甲基)苯基的类固醇化合物，一种具有终端氟化烷基团的磷脂酰丝氨酸化合物，一种具有双(三氟甲基苯基的甘油酯化合物，或一种具有终端氟化烷基团的甘油酯化合物。通过使用含有该化合物或其盐的脂质体的造影剂，可以选择性地成像血管病变。