Boc-L-烯丙基甘氨酸 | 90600-20-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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: Boc-L-烯丙基甘氨酸
• 中文别名: 叔丁氧羰基-L-烯丙基甘氨酸；(S)-N-BOC-烯丙基甘氨酸；N-Boc-L-烯丙基甘氨酸；(S)-2-烯丙基-Boc-甘氨酸
• 英文名称: (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid
• 英文别名: (S)-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid；(S)-N-Boc-allylglycine；Boc-L-allylglycine；N-Boc-allylglycine；N-Boc-L-allylglycine；(S)-2-tert-butoxycarbonylamino-4-pentenoic acid；L-Boc-allylglycine；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid
• CAS: 90600-20-7
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: BUPDPLXLAKNJMI-ZETCQYMHSA-N

物化性质

• 沸点：
  355.52°C (rough estimate)
• 比旋光度：
  10.5 º (c=1, methanol)
• 密度：
  1.1835 (rough estimate)
• 溶解度：
  可溶于氯仿、甲醇
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 海关编码：
  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：
  存放在阴凉干燥处即可。

SDS

Name:	(S)-N-BOC-Allylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	(S)-N-tert-Butoxycarbonyl-2-Amino-4-Pentenoic Acid
CAS:	90600-20-7

Section 1 - Chemical Product MSDS Name:(S)-N-BOC-Allylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:(S)-N-tert-Butoxycarbonyl-2-Amino-4-Pentenoic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
90600-20-7	(S)-N-BOC-Allylglycine	95%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 90600-20-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Viscous liquid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H17NO4
Molecular Weight: 215.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 90600-20-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-BOC-Allylglycine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 90600-20-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 90600-20-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 90600-20-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

(S)-2-((叔丁氧羰基)氨基)戊-4-烯酸是甘氨酸（HY-Y0966）的衍生物[1]。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  N-Boc-L-烯丙基甘氨酸甲酯	methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate	89985-87-5	C11H19NO4	229.276
  ——	ethyl (RS)-N-(tert-butoxycarbonyl)-2-aminopent-4-enoate	135722-56-4	C12H21NO4	243.303
  ——	tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate	151436-20-3	C14H25NO4	271.357
  ——	methyl 2-[((1,1-dimethylethoxy)carbonyl)amino]-4-pentynoate	71460-02-1	C11H17NO4	227.26
  Boc-L-天冬氨酸 4-甲酯	(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester	59768-74-0	C10H17NO6	247.248
  (R)-N-叔丁氧羰基-3-碘代丙氨酸甲酯	N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester	93267-04-0	C9H16INO4	329.135
  ——	(S)-2-Boc-aziridine-2-carboxylic acid	181212-91-9	C8H13NO4	187.196

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  N-Boc-L-烯丙基甘氨酸甲酯	methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate	89985-87-5	C11H19NO4	229.276
  ——	ethyl (S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate	——	C12H21NO4	243.303
  ——	N-α-Boc-allylglycinal	95107-99-6	C10H17NO3	199.25
  ——	(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pent-4-enoic acid	136092-76-7	C11H19NO4	229.276
  ——	(S)-tert-butyl (1-hydroxypent-4-en-2-yl)carbamate	——	C10H19NO3	201.266
  ——	tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate	151436-20-3	C14H25NO4	271.357
  (S)-2-((叔丁氧羰基)氨基)庚-6-烯酸	(S)-2-tert-butoxycarbonylamino-hept-6-enoic acid	204711-97-7	C12H21NO4	243.303
  ——	cyclopentyl (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate	1021943-48-5	C15H25NO4	283.368
  ——	(S)-3-[N-[(tert-butyloxy)carbonyl]amino]-5-hexen-2-one	219990-12-2	C11H19NO3	213.277
  ——	(2S)-2-tert-butoxycarbonylamino-6-methylheptanoic acid methyl ester	329270-48-6	C14H27NO4	273.373

反应信息

• 作为反应物：
  描述：

  Boc-L-烯丙基甘氨酸 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 camphor-10-sulfonic acid 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 二甲基亚砜 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 113.5h， 生成 L-羟基脯氨酸
  参考文献：
  名称：

  棘白菌素的全合成。I. 组成氨基酸的立体控制合成

  摘要：

  图 1. (a) 嘧啶并 [5,4-g] 蝶啶 N-氧化物 1 (5 XM) 在 MeCN 中的紫外-可见吸收光谱。(b) 1 (5 m M ) 和 DMA (250 m M ) 与 1 (5 m M ) 在 MeCN 中的混合物的差异光谱。(c) 1 (5 m M ) 和 DMA (50 m M ) 在 MeCN 中的 1 (5 m M ) 和 DMA (50 m M ) 溶液用光栅单色仪（JASCO 模型）照射CRM-FA) 与 2-kW Xe 灯和 4-nm 带宽在氩气气氛下持续 2 小时。

  DOI：

  10.1021/ja00279a064
• 作为产物：
  描述：

  (S)-(-)-2-氨基-4-戊烯酸 生成 Boc-L-烯丙基甘氨酸
  参考文献：
  名称：

  Rapid syntheses of 3-amino-5-hydroxymethyl-γ-lactones from L-allylglycine

  摘要：

  (3R,5R)和(3R,5S) N-保护γ-内酯3-氨基-5-羟甲基酯通过甲基N-保护的L-丙二醇甘氨酸酯的一个二羟化步骤获得。 © 1998 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(98)00697-2

文献信息

• [EN] PROTEIN TYROSINE PHOSPHATASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE PROTÉINE TYROSINE PHOSPHATASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CALICO LIFE SCIENCES LLC

  公开号：WO2020186199A1

  公开（公告）日：2020-09-17

  Provided herein are compounds, compositions, and methods useful for inhibiting protein tyrosine phosphatase, e.g., protein tyrosine phosphatase non-receptor type 2 (PTPN2) and/or protein tyrosine phosphatase non-receptor type 1 (PTPN1), and for treating related diseases, disorders and conditions favorably responsive to PTPN 1 or PTPN2 inhibitor treatment, e.g., a cancer or a metabolic disease.

  本文提供了用于抑制蛋白酪氨酸磷酸酶的化合物、组合物和方法，例如蛋白酪氨酸磷酸酶非受体型2（PTPN2）和/或蛋白酪氨酸磷酸酶非受体型1（PTPN1），以及用于治疗对PTPN1或PTPN2抑制剂治疗有良好反应的相关疾病、紊乱和状况的方法，例如癌症或代谢性疾病。
• Methylene Analogues of Neopetrosiamide as Potential Antimetastatic Agents: Solid-Supported Syntheses Using Diamino Diacids for Pre-Stapling of Peptides with Multiple Disulfides
  作者：Cameron A. Pascoe、Daniel B. Engelhardt、Albert Remus R. Rosana、Marco J. van Belkum、John C. Vederas

  DOI：10.1021/acs.orglett.1c03532

  日期：2021.12.3

  Neopetrosiamide, a 28-residue peptide from Neopetrosia sp., contains three disulfide bonds and hinders mammalian tumor cell invasion. Proper connectivity of disulfide bonds is crucial for activity. Synthetic replacement of single disulfide bridges with methylene bridges gives active analogues. Pre-stapling of one ring enhances the correct formation of the remaining disulfides by reducing isomeric possibilities

  Neopetrosiamide 是一种来自Neopetrosia sp. 的 28 个残基肽，含有三个二硫键，可阻碍哺乳动物肿瘤细胞的侵袭。二硫键的正确连接对于活性至关重要。用亚甲基桥合成取代单个二硫桥得到活性类似物。一个环的预钉合通过减少异构体的可能性并可能启动正确的 3D 折叠来增强剩余二硫化物的正确形成。新石油酰胺在大肠杆菌中的克隆和表达提供了获得天然线性肽的途径。
• [EN] BENZIMIDAZOLE ANTIVIRAL AGENTS<br/>[FR] AGENTS ANTIVIRAUX À BASE DE BENZIMIDAZOLE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011097491A1

  公开（公告）日：2011-08-11

  Provided are compounds of Formula (I) and (II) and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

  提供的是公式(I)和(II)的化合物以及它们的药用可接受盐，它们的药物组合物，它们的制备方法，以及它们用于治疗由黄病毒科病毒家族成员如丙型肝炎病毒（HCV）介导的病毒感染。
• Pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis
  作者：Nourdin Ghalit、Dirk T. S. Rijkers、Johan Kemmink、Cees Versluis、Rob M. J. Liskamp

  DOI：10.1039/b415555f

  日期：——

  An alkene-bridged mimic of the complex DE-bisthioether-ring system of the antibiotic nisin was prepared in one step from the linear precursor.

  一步法合成了一种烯烃桥接的仿生抗生素nisin复合物DE-双硫醚环系统的模拟物，该模拟物源自线性前体。
• [EN] DIAMIDE MACROCYCLES AS FACTOR XIA INHIBITORS<br/>[FR] MACROCYCLES DIAMIDES UTILISÉS EN TANT QU'INHIBITEURS DU FACTEUR XIA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016205482A1

  公开（公告）日：2016-12-22

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective factor XIa inhibitors or dual inhibitors of FXIa and plasma kallikrein. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.

  本发明提供了式(I)的化合物：或其立体异构体、互变异构体或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性因子XIa抑制剂或FXIa和血浆激肽酶的双重抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用它们治疗血栓栓塞和/或炎症性疾病的方法。