（s）-2,3-二羟基丙酸甲酯 | 10303-88-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: （s）-2,3-二羟基丙酸甲酯
• 中文别名: (S)-2,3-二甲基丙酸甲酯；L-(+)-甘油酸甲酯；(S)-2,3-二羟基丙酸甲酯；(+)-甘油酸甲酯
• 英文名称: methyl L-glycerate
• 英文别名: L-glyceric acid methyl ester；methyl (S)-glycerate；methyl (S)-2,3-dihydroxypropanoate；(S)-methyl 2,3-dihydroxypropanoate；methyl (S)-2,3-dihydroxypropionate；methyl (2S)-2,3-dihydroxypropanoate
• CAS: 10303-88-5
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: COFCNNXZXGCREM-VKHMYHEASA-N

物化性质

• 沸点：
  241.5±0.0℃ (760 Torr)
• 密度：
  1.285±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  103.7±11.7℃

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918199090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-Methyl 2,3-dihydroxypropanoate
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: (S)-Methyl 2,3-dihydroxypropanoate
CAS number: 10303-88-5

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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: C4H8O4
Molecular weight: 120.1

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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.

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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

反应信息

• 作为反应物：
  描述：

  （s）-2,3-二羟基丙酸甲酯 在 barium dihydroxide 作用下， 以 水 为溶剂， 生成 (S)-2,3-dihydroxypropanoic acid hemicalcium salt
  参考文献：
  名称：

  （R）-（S）-O-异丙基-1,2-甘油酯的合成。确定纯净度

  摘要：

  （R）-和（S）-甘油丙酮酸酯的合成。光学纯度的测定

  DOI：

  10.1002/hlca.19850680708
• 作为产物：
  描述：

  L-丝氨酸 生成 （s）-2,3-二羟基丙酸甲酯
  参考文献：
  名称：

  氨基酸作为手性合成子：对映体纯的α-羟基酯的合成。

  摘要：

  高碳酸锂与衍生自天冬氨酸的α-羟基β-溴代酯反应，得到高对映体纯度的α-羟基酯。

  DOI：

  10.1016/0040-4039(84)80110-0

文献信息

• [EN] ARYLMETHYLENE HETEROCYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES D'ARYLMÉTHYLÈNE UTILISÉS EN TANT QUE BLOQUEURS DES CANAUX POTASSIQUES KV1.3 DE TYPE SHAKER
  申请人：DE SHAW RES LLC

  公开号：WO2021071806A1

  公开（公告）日：2021-04-15

  A compound of Formula (I) or a pharmaceutically acceptable salt thereof is described, wherein the substituents are as defined herein. Pharmaceutical compositions comprising the same and method of using the same are also described.

  描述了化合物的公式（I）或其药学上可接受的盐，其中取代基如本文所定义。还描述了包含相同化合物的药物组合物以及使用该药物的方法。
• Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)Co^III Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols
  作者：Scott E. Schaus、Bridget D. Brandes、Jay F. Larrow、Makoto Tokunaga、Karl B. Hansen、Alexandra E. Gould、Michael E. Furrow、Eric N. Jacobsen

  DOI：10.1021/ja016737l

  日期：2002.2.1

  The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)Co(III) complex 1 x OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several

  由手性 (salen)Co(III) 配合物 1 x OAc 催化的末端环氧化物的水解动力学拆分 (HKR) 提供了回收的未反应环氧化物和高度对映体富集形式的 1,2-二醇产物。因此，HKR 提供了从廉价的外消旋材料中获得有用的、高度对映体富集的手性结构单元的通用途径，而这些结构单元在其他方面难以获得。从实用的角度来看，该反应具有几个吸引人的特点，包括使用 H(2)O 作为反应物和低负载 (0.2-2.0 mol%) 的可回收、市售催化剂。此外，HKR 显示出非凡的范围，因为可以将各种空间和电子变化的环氧化物分解为 > 或 = 99% ee。相应的 1,2-二醇是使用 0.45 当量的 H(2)O 在良好到高对映体过量中产生的。提供了用于分离高度对映体富集的环氧化物和二醇以及催化剂回收和再循环的有用和通用的协议。HKR 反应的选择性因子 (k(rel)) 通过测量约 ee 的产物 ee 来确定。20%
• Total Synthesis of (+)-Migrastatin
  作者：Sébastien Reymond、Janine Cossy

  DOI：10.1002/ejoc.200600760

  日期：2006.11

  (+)-Migrastatin, an antimetastatic agent, was synthesized by using three ruthenium-catalyzed metathesis reactions: a ring-closing metathesis (RCM) to control the (Z)-trisubstituted double bond at C11–C12, another RCM at C6–C7 to establish the macrolactone core, and a cross-metathesis to install the glutarimide side chain at C16–C17. The stereogenic centers at C9, C10, C13, and C14 were introduced by

  (+)-Migrastatin 是一种抗转移剂，通过使用三种钌催化的复分解反应合成：闭环复分解 (RCM) 控制 C11-C12 的 (Z)-三取代双键，另一个 RCM 在 C6-C7建立大环内酯核心，并通过交叉复分解在 C16-C17 上安装戊二酰亚胺侧链。C9、C10、C13 和 C14 的立体中心是通过使用两个立体选择性巴豆金属化引入的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Hydrolytic Kinetic Resolution of Epoxides Catalyzed by Chromium(III)-endo,endo-2,5-diaminonorbornane-salen [Cr(III)-DIANANE-salen] Complexes. Improved Activity, Low Catalyst Loading
  作者：Albrecht Berkessel、Erkan Ertürk

  DOI：10.1002/adsc.200606181

  日期：2006.12

  The hydrolytic kinetic resolution (HKR) of terminal epoxides, using chiral chromium(III)-salen catalysts based on DIANANE (endo,endo-2,5-diaminonorbornane), was studied. A broad substrate scope was found for the chromium(III)-DIANANE catalysts, and very low loadings (down to 0.05 mol %) were needed to achieve high enantiomeric purities of both the remaining epoxides and the product diols (up to >99 %

  研究了基于DIANANE（内，内--2,5-二氨基降冰片烷）的手性铬（III）-salen催化剂对末端环氧化物的水解动力学拆分（HKR）。发现铬（III）-二亚胺催化剂具有广泛的底物范围，并且需要极低的负载量（低至0.05 mol％）以实现剩余的环氧化物和产物二醇的高对映体纯度（最高> 99％ee））。除单取代的环氧化物外，在电子调谐的铬（III）-二亚胺的存在下，可以以不对称的方式用水将2-甲基-2-正戊基环氧乙烷（2,2-二取代的环氧化物的一个例子）开环。复杂的。
• Synthesis and biological evaluation of enantiomerically pure glyceric acid derivatives as LpxC inhibitors
  作者：Giovanni Tangherlini、Tullio Torregrossa、Oriana Agoglitta、Jens Köhler、Jelena Melesina、Wolfgang Sippl、Ralph Holl

  DOI：10.1016/j.bmc.2016.01.029

  日期：2016.3

  the inhibitory activity against LpxC, glyceric acid ethers (R)-7a, (S)-7a, (R)-7b, and (S)-7b, lacking the hydroxymethyl group in benzylic position, were synthesized. The compounds were obtained in enantiomerically pure form by a chiral pool synthesis and a lipase-catalyzed enantioselective desymmetrization, respectively. The enantiomeric hydroxamic acids (R)-7b (Ki = 230 nM) and (S)-7b (Ki = 390 nM)

  UDP-3-O-[（R）-3-羟基肉豆蔻酰基] -N-乙酰氨基葡糖脱乙酰酶（LpxC）的抑制剂代表了一种有前途的新型抗生素，可以选择性地对抗革兰氏阴性菌。为了阐明二醇的羟甲基（冲击小号，小号） - 4关于对LpxC，甘油酸醚（抑制活性- [R ）-图7a，（小号） -图7a，（- [R ）-图7b，和（小号）-7b合成了在苄基位置上没有羟甲基的化合物。通过手性库合成和脂肪酶催化的对映选择性去对称化分别以对映体纯的形式获得化合物。对映异构体异羟肟酸（R）-7b（K i  = 230 nM）和（S）-7b（K i  = 390 nM）显示出有希望的酶抑制作用。但是，它们的抑制活性彼此之间基本上没有区别，从而导致低的eudymic比率。通常，合成的甘油酸衍生物7对两种大肠杆菌显示出抗菌活性。超过各自区域异构体的菌株6。