(1R,2S,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯 | 321744-17-6

• 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: (1R,2S,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯
• 英文名称: (1R,3R,4S)-3-tert-butoxycarbonylamino-4-hydroxycyclopentanecarboxylic acid methyl ester
• 英文别名: N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(R)-carboxylic acid methyl ester；(1R,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester；methyl (1R,3S,4R)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate
• CAS: 321744-17-6
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: SSATZBUCOTXXGA-HLTSFMKQSA-N

物化性质

• 沸点：
  402.56°C (rough estimate)
• 密度：
  1.1623 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• 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

• 安全说明：
  S24/25

SDS

Name:	(1R 2S 4R)-N-BOC-1-Amino-2-Hydroxycyclopentane-4-Carboxylic Acid Material Safety Data Sheet
Synonym:	Methyl (1R,3R,4S)-N-BOC-3-Amino-4-Hydroxycyclopentanecarboxylate
CAS:	321744-17-6

Section 1 - Chemical Product MSDS Name:(1R 2S 4R)-N-BOC-1-Amino-2-Hydroxycyclopentane-4-Carboxylic Acid Material Safety Data Sheet
Synonym:Methyl (1R,3R,4S)-N-BOC-3-Amino-4-Hydroxycyclopentanecarboxylate

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
321744-17-6	(1R,2S,4R)-N-BOC-1-Amino-2-Hydroxycycl	95%	unlisted

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

---

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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

---

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.

---

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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. 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 cool, dry place. Store in a tightly closed container.

---

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# 321744-17-6: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
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: C12H21NO5
Molecular Weight: 259.3

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 321744-17-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1R,2S,4R)-N-BOC-1-Amino-2-Hydroxycyclopentane-4-Carboxylic - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

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# 321744-17-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 321744-17-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 321744-17-6 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯 在 4-二甲氨基吡啶 、 TEA 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 197.0h， 生成 (1R,3R,4R)-3-Acetoxy-4-tert-butoxycarbonylamino-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffold for drug discovery

  摘要：

  A route to all eight stereoisomers of 3-(tert-butoxycarbonylamino)-4-hydroxycyclopentanecarboxylic acid methyl ester is presented; these products should prove to be valuable scaffolds in pharmaceutical discovery. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00108-2
• 作为产物：
  描述：

  (1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐 在 (+)-1,2-bis((2R,5R)-2,5-dimethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate Oxone 、 TEA 、 氢气 、 四丁基硫酸氢铵 、 edetate disodium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 、 丙酮 为溶剂， 反应 37.0h， 生成 (1R,2S,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯
  参考文献：
  名称：

  对映纯4-（叔丁氧基羰基氨基）环戊-1-烯羧酸甲酯的高选择性定向氢化

  摘要：

  同时使用的ñ -叔叔丁氧羰和羟基定向加氢方法得到的3-基本上单非对映体（叔丁氧基羰基）-4- hydroxycyclopentanecarboxylic酸甲酯和3-（叔丁氧基羰基）环戊烷羧酸甲酯进行说明。这些结果结合了第一个报道的官能化环戊烯的氨基甲酸酯定向加氢反应。

  DOI：

  10.1016/s0040-4039(00)02210-3

文献信息

• [EN] ANTIBACTERIAL AMINOGLYCOSIDE ANALOGS<br/>[FR] ANALOGUES D'AMINOGLYCOSIDES ANTIBACTÉRIENS
  申请人：ACHAOGEN INC

  公开号：WO2009067692A1

  公开（公告）日：2009-05-28

  Compounds of structure (I): having antibacterial activity are disclosed, including stereoisomers, pharmaceutically acceptable salts and prodrugs thereof, wherein Q1, Q2, Q3, R8 and R9 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

  结构（I）的化合物具有抗菌活性，包括立体异构体、药用可接受的盐和前药，其中Q1、Q2、Q3、R8和R9如本文所定义。还公开了与制备和使用这些化合物相关的方法，以及包含这些化合物的药物组合物。
• Use of hydrolases for the synthesis of cyclic amino acids
  作者：Richard C Lloyd、Michael C Lloyd、Mark E.B Smith、Karen E Holt、Jonathan P Swift、Philip A Keene、Stephen J.C Taylor、Raymond McCague

  DOI：10.1016/j.tet.2003.10.116

  日期：2004.1

  The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. In order to elaborate these building blocks into more complex molecules, crystallization and asymmetric hydrogenation were used to define further stereocentres

  描述了具有所有必要结构特征以使其成为用于药物化学的理想支架的几种环状氨基酸的合成。每个合成过程中的关键步骤是使用水解酶来定义手性中心。为了将这些结构单元详细化为更复杂的分子，使用了结晶和不对称氢化来定义进一步的立体中心。
• Substituted cyclopentenes, their preparation and their use for chiral scaffolds
  申请人：ChirotechTechnology Limited

  公开号：US06593489B1

  公开（公告）日：2003-07-15

  3,4-Disubstituted-1-cyclopentene compounds, in substantially enantiopure form, have the relative stereochemistry according to formula (1A) or (1B) including the opposite enantiomers thereof, wherein R1 is either COOX, wherein X is selected from the group consisting of alkyl, H, and a salt-forming cation, or CH2OH, whererin the hydroxy group is optionally protected; R2 is H or a protecting group; R3 is H or alkyl, and R4 is selected from the group consisting of H, alkoxy, alkyl, aryl, and aralkyl; or, in the case of formula (1A), R2 and R4 are linked to form an oxazolidonone ring. These compounds can be used to prepare a series of complementary stereochemcially varied cyclopentane scaffolds.

  3,4-二取代-1-环戊烯化合物，以实质性对映纯形式存在，具有相对立体化学式（1A）或（1B），包括其相反的对映异构体，其中R1为COOX，其中X选自烷基，H和盐形成阳离子的组成群；或为CH2OH，其中羟基基团可以选择性地保护；R2为H或保护基；R3为H或烷基，R4选自H，烷氧基，烷基，芳基和芳基烷基；或在公式（1A）中，R2和R4连接形成噁唑烷酮环。这些化合物可用于制备一系列互补的立体化学变化的环戊烷支架。
• US6593489B1
  申请人：——

  公开号：US6593489B1

  公开（公告）日：2003-07-15
• An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffold for drug discovery
  作者：Mark E.B. Smith、Michael C. Lloyd、Nadine Derrien、Richard C. Lloyd、Stephen J.C. Taylor、David A. Chaplin、Guy Casy、Raymond McCague

  DOI：10.1016/s0957-4166(01)00108-2

  日期：2001.4

  A route to all eight stereoisomers of 3-(tert-butoxycarbonylamino)-4-hydroxycyclopentanecarboxylic acid methyl ester is presented; these products should prove to be valuable scaffolds in pharmaceutical discovery. (C) 2001 Elsevier Science Ltd. All rights reserved.