(2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid | 130930-25-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 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: (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
• 英文别名: (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid；(2R,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 130930-25-5
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: WWVCWLBEARZMAH-GHMZBOCLSA-N

物化性质

• 沸点：
  486.9±45.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-D-Cis-Hyp-OH
Synonyms: (2R,4R)-1-[(Benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

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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: Z-D-Cis-Hyp-OH
CAS number: 130930-25-5

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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: C13H15NO5
Molecular weight: 265.3

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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

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  (2R,4S)-4-羟基-1-苯基甲氧基羰基吡咯烷-2-羧酸	(4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline	155153-78-9	C13H15NO5	265.266
  N-CBZ-顺式-4-羟基-D-脯氨酸甲酯	(2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate	155075-23-3	C14H17NO5	279.293
  N-苄氧羰基-反式-4-羟基-D-脯氨酸甲酯	1-benzyl 2-methyl (2R,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate	79433-95-7	C14H17NO5	279.293
  ——	(2R,4R)-1-(benzyloxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid	200184-91-4	C14H17NO5	279.293
  ——	(2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine	130930-27-7	C15H19NO5	293.32
  ——	(2R,4R)-1-[(benzyloxy)carbonyl]-4-(hexyloxy)pyrrolidine-2-carboxylic acid	——	C19H27NO5	349.427
  ——	(2R,4S)-1-(Benzyloxycarbonyl)-4-hydroxyproline tert-butyl ester	159487-62-4	C17H23NO5	321.373
  ——	N-benzyloxycarbonyl-cis-4-hydroxy-L-prolinol	1009335-39-0	C13H17NO4	251.282
  ——	(2S,4R)-1-(benzyloxycarbonyl)-4-(4-methoxybenzyloxy)pyrrolidine-2-carboxylic acid	1194056-65-9	C21H23NO6	385.417
  ——	cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline	329188-63-8	C19H29NO5Si	379.528

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 在 Jones reagent 、 硫酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 1-benzyl-2-(tert-butyl) (R)-4-oxopyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  一种改进的，可扩展的双氨基酸合成

  摘要：

  反式-4-羟基-1-脯氨酸衍生的双氨基酸是手性的环状结构单元，显示出两个带有保护基的α-氨基酸。它们被组装成螺线低聚物—刚性，形状可编程的螺环低聚物，在立体化学和功能上都不同。这里提出的合成集中在最近的改进上，这些改进允许从便宜的反式-4-羟基-1-脯氨酸方便，大规模地合成十二种立体化学纯的双氨基酸。双氨基酸在立体化学上和胺保护基上有所不同，其中一个（对硝基苄基氨基甲酸酯）以前没有被掺入双氨基酸中。

  DOI：

  10.1016/j.tetlet.2016.09.032
• 作为产物：
  描述：

  L-羟基脯氨酸 在 乙酸酐 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 反应 48.0h， 生成 (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  一种改进的，可扩展的双氨基酸合成

  摘要：

  反式-4-羟基-1-脯氨酸衍生的双氨基酸是手性的环状结构单元，显示出两个带有保护基的α-氨基酸。它们被组装成螺线低聚物—刚性，形状可编程的螺环低聚物，在立体化学和功能上都不同。这里提出的合成集中在最近的改进上，这些改进允许从便宜的反式-4-羟基-1-脯氨酸方便，大规模地合成十二种立体化学纯的双氨基酸。双氨基酸在立体化学上和胺保护基上有所不同，其中一个（对硝基苄基氨基甲酸酯）以前没有被掺入双氨基酸中。

  DOI：

  10.1016/j.tetlet.2016.09.032

文献信息

• Methods for Production of Optically Active Fluoropyrrolidine Derivatives
  申请人：Umemoto Teruo

  公开号：US20100174096A1

  公开（公告）日：2010-07-08

  Useful industrial methods for producing optically active fluoropyrrolidine derivatives as useful fluorinated intermediates are disclosed.

  揭示了用于生产光学活性氟吡咯烷衍生物的有用工业方法，作为有用的氟化中间体。
• Structure guided design of a series of sphingosine kinase (SphK) inhibitors
  作者：Darin J. Gustin、Yihong Li、Matthew L. Brown、Xiaoshan Min、Mike J. Schmitt、Malgorzata Wanska、Xiaodong Wang、Richard Connors、Sheere Johnstone、Mario Cardozo、Alan C. Cheng、Shawn Jeffries、Brendon Franks、Shyun Li、Shanling Shen、Mariwil Wong、Holger Wesche、Guifen Xu、Timothy J. Carlson、Matthew Plant、Kurt Morgenstern、Karen Rex、Joanna Schmitt、Angela Coxon、Nigel Walker、Frank Kayser、Zhulun Wang

  DOI：10.1016/j.bmcl.2013.06.030

  日期：2013.8

  inhibition of both isoforms is likely required to block SphK dependent angiogenesis. A structure based approach was used to design and synthesize a series of SphK inhibitors resulting in the identification of the first potent inhibitors of both isoforms of human SphK. Additionally, to our knowledge, this series of inhibitors contains the only sufficiently potent inhibitors of murine SphK1 with suitable

  鞘氨醇-1-磷酸（S1P）信号在有丝分裂，细胞迁移和血管生成中起着至关重要的作用。鞘氨醇激酶（SphKs）催化鞘磷脂代谢中的关键步骤，从而导致S1P的产生。SphK有两种同工型，对SphK缺陷小鼠的观察表明，这两种同工型可以弥补彼此的损失。因此，可能需要抑制两种同工型才能阻断SphK依赖性血管生成。基于结构的方法用于设计和合成一系列SphK抑制剂，从而鉴定出人类SphK两种同工型的第一种有效抑制剂。此外，据我们所知，
• 4.5-diaryloxazole compounds with prostaglandin I2 (PGI2) agonistic activity
  申请人：Fujisawa Pharmaceutical Co. Ltd.

  公开号：US06660759B1

  公开（公告）日：2003-12-09

  Heterocyclic compounds of formula (I), wherein R1 is carboxy or protected carboxy, R2 is aryl which may have suitable sustituent(s), R3 is aryl which may have suitable substituent(s), R4 is hydrogen, lower alkyl, hydroxy or aryl, A1 is lower alkylene, (a) is (b), etc., —A3— is (c), etc. and n is 0 or 1, and pharmaceutically acceptable salts thereof which are useful as a medicament.

  式（I）的杂环化合物，其中R1是羧基或保护羧基，R2是可能带有适当取代基的芳基，R3是可能带有适当取代基的芳基，R4是氢、低碳基、羟基或芳基，A1是低碳烯基，（a）是（b），等等，—A3—是（c），等等。n为0或1，以及其药学上可接受的盐，可用作药物。
• [EN] HYDROXAMATE-BASED INHIBITORS OF DEACETYLASES<br/>[FR] COMPOSÉS À BASE D'HYDROXAMATE EN TANT QU'INHIBITEURS DES DÉSACÉTYLASES
  申请人：NOVARTIS AG

  公开号：WO2012025164A1

  公开（公告）日：2012-03-01

  The present teachings relate to compounds of Formula (I): and pharmaceutically acceptable salts, hydrates, esters, and prodrugs thereof, wherein R1, R2, R3, R4, R5, ring A, and Z are as defined herein. The present teachings also provide methods of preparing compounds of Formula (I) and methods of use compounds of Formula (I) in treating pathologic conditions or disorders mediated wholly or in part by deacetylases.

  本教导涉及公式（I）的化合物及其药用盐、水合物、酯和前药，其中R1、R2、R3、R4、R5、环A和Z如本文所定义。本教导还提供制备公式（I）化合物的方法，以及利用公式（I）化合物治疗完全或部分由脱乙酰酶介导的病理状况或疾病的方法。
• Chemoselective Synthesis of<i>N</i>-Protected Alkoxyprolines under Specific Solvation Conditions
  作者：Voichita Mihali、Francesca Foschi、Michele Penso、Gianluca Pozzi

  DOI：10.1002/ejoc.201402429

  日期：2014.8

  N-Protected hydroxyprolines (Hyp) were transformed chemoselectively into alkoxyproline derivatives by direct O-alkylation. The starting Hyp was transformed into the corresponding dianion in a mixture of dimethyl sulfoxide and tetrahydrofuran (1:16 v/v) as solvent. Under these conditions, the carboxy-anion showed reduced nucleophilicity because it was specifically solvated, and the more reactive oxy-anion

  N-保护的羟脯氨酸 (Hyp) 通过直接 O-烷基化被化学选择性地转化为烷氧基脯氨酸衍生物。在作为溶剂的二甲基亚砜和四氢呋喃 (1:16 v/v) 的混合物中，起始的 Hyp 被转化为相应的二价阴离子。在这些条件下，羧基阴离子显示出降低的亲核性，因为它被特异性地溶剂化，而更具反应性的氧阴离子被选择性地烷基化。N-保护的反-4-烷氧基-、顺-4-烷氧基-和反-3-烷氧基脯氨酸因此以非常高的总产率和立体中心构型的完全稳定性在单个步骤中获得。