(+)-(R)-ethyl 4-benzyloxy-3-hydroxybutanoate | 106058-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(R)-ethyl 4-benzyloxy-3-hydroxybutanoate
• 英文别名: (3R)-ethyl 4-benzyloxy-3-hydroxybutanoate；ethyl (R)-4-benzyloxy-3-hydroxybutanoate；ethyl (R)-4-benzyloxy-3-hydroxybutyrate；ethyl(R)-4-benzyloxy-3-hydroxybutyrate；ethyl (3R)-3-hydroxy-4-phenylmethoxybutanoate
• CAS: 106058-91-7
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: HMHGAAZSPNXMCQ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

SDS

Name:	Ethyl (R)-4-benzyloxy-3-hydroxybutyrate Material Safety Data Sheet
Synonym:
CAS:	106058-91-7

Section 1 - Chemical Product MSDS Name:Ethyl (R)-4-benzyloxy-3-hydroxybutyrate Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
106058-91-7	Ethyl (R)-4-benzyloxy-3-hydroxybutyrat		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 106058-91-7: Personal Protective Equipment Eyes: Not available.
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: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 160 - 162 deg C @ 5
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: C13H18O4
Molecular Weight: 238.28

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 106058-91-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl (R)-4-benzyloxy-3-hydroxybutyrate - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 106058-91-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 106058-91-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 106058-91-7 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

反应信息

• 作为反应物：
  描述：

  (+)-(R)-ethyl 4-benzyloxy-3-hydroxybutanoate 在 钯 氢气 作用下， 以 甲醇 为溶剂， 以93%的产率得到(+)-(R)-ethyl 3,4-dihydroxybutanoate
  参考文献：
  名称：

  Manzocchi, Ada; Casati, Rosangela; Fiecchi, Alberto, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2753 - 2758

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 4-(benzyloxy)-2-chloro-3-oxobutanoate 在 palladium on activated charcoal potassium phosphate buffer 、 Tween 80 、 乙醇 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 27.0 ℃ 、101.33 kPa 条件下， 反应 25.5h， 生成 (+)-(R)-ethyl 4-benzyloxy-3-hydroxybutanoate
  参考文献：
  名称：

  The microbial reduction of 2-chloro-3-oxoesters

  摘要：

  Several aliphatic or aromatic 2-chloro-3-oxoesters are stereoselectively reduced by yeast or fungal strains, affording in fair to good yield and high enantiomeric excess some of the respective 2-chloro-3-hydroxyester stereoisomers.

  DOI：

  10.1016/0957-4166(95)00294-y

文献信息

• Control of Enantioselectivity in the Bakers' Yeast Reduction of β-Keto Ester Derivatives in the Presence of a Sulfur Compound
  作者：Ryuuichirou Hayakawa、Kazumi Nozawa、Makoto Shimizu、Tamotsu Fujisawa

  DOI：10.1016/s0040-4039(97)10490-7

  日期：1998.1

  Improvement of the enantioselectivity and enhancement of the reactivity were achieved in the bakers' yeast reduction of the β-keto ester derivatives by the addition of a sulfur compound. © 1997 Elsevier Science Ltd. All rights reserved.

  通过添加硫化合物，在面包师的酵母还原β-酮酯衍生物中，实现了对映选择性的提高和反应性的提高。©1997 Elsevier ScienceLtd。保留所有权利。
• The bakers' yeast reductions of α- and β-keto ester derivatives in the presence of a sulfur compound
  作者：Ryuuichirou Hayakawa、Kazumi Nozawa、Kimihiko Kimura、Makoto Shimizu

  DOI：10.1016/s0040-4020(99)00373-7

  日期：1999.6

  enhancement of the reactivity were achieved in the bakers' yeast reduction of the α- and β-keto ester derivatives by the addition of a sulfur compound. High enantioselectivity in the bakers' yeast reduction of keto esters was accomplished by using combination of an addition of a sulfur compound with an appropriate selection of the alcohol part of the ester.

  通过添加硫化合物，在面包师的酵母还原α-和β-酮酯衍生物中，实现了对映选择性的提高和反应性的提高。在面包酵母还原酮酯的对映体选择性高，通过使用加硫化合物与酯的醇部分的适当选择的组合来实现。
• An Efficient Ruthenium-Catalyzed Formal Synthesis of (−)-Isoavenaciolide
  作者：Olivier Labeeuw、Delphine Blanc、Phannarath Phansavath、Virginie Ratovelomanana-Vidal、Jean-Pierre Genêt

  DOI：10.1002/ejoc.200400047

  日期：2004.6

  (−)-isoavenaciolide (1), features the stereoselective construction of the three contiguous stereogenic centers by Evans diastereoselective reduction (d.e. = 80%) of β-hydroxy ketone 8. In the more efficient second approach, the nine-step sequence leading to the key precursor 2 involves sequential ruthenium-catalyzed hydrogenation reactions of β-keto ester 4 and β-hydroxy ketone 14 to form the two hydroxyl

  报道了通过两种不同途径正式合成 (-)-isoavenaciolide (1)。第一种方法产生了 (-)-isoavenaciolide (1) 的关键前体 2，其特征是通过 β-羟基酮 8 的 Evans 非对映选择性还原（de = 80%）对三个连续的立体中心进行立体选择性构建。有效的第二种方法，导致关键前体 2 的九步序列涉及连续钌催化的 β-酮酯 4 和 β-羟基酮 14 氢化反应形成两个羟基，并具有极好的反立体化学控制（de = 99%）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Process for producing optically active gamma-butyrolactone
  申请人：——

  公开号：US20030105341A1

  公开（公告）日：2003-06-05

  This invention provides a novel process for producing optically active 3-hydroxy-&ggr;-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-&ggr;-butyrolactone represented by formula I: 1 wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: 2 wherein R 1 represents a C 1-4 lower alkyl group, R 2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

  本发明提供了一种新的生产光学活性3-羟基-γ-丁内酯的工艺，该工艺步骤短，经济高效，适合工业应用，使用的起始材料廉价易得，试剂易于处理。本发明涉及一种生产光学活性3-羟基-γ-丁内酯的工艺，其化学式为I:1，其中符号*表示不对称碳原子，包括在异质催化剂和酸性物质的存在下，氢化化合式II:2所代表的光学活性4-取代氧基-3-羟基丁酸酯，其中R1表示C1-4较低烷基基团，R2表示羟基的保护基，通过脱保护和同时环闭反应。
• Process for producing optically active &ggr;-butyrolactone
  申请人：Takasago International Corporation

  公开号：US06608214B2

  公开（公告）日：2003-08-19

  This invention provides a novel process for producing optically active 3-hydroxy-&ggr;-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-&ggr;-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

  本发明提供了一种生产光学活性3-羟基-γ-丁内酯的新工艺，在使用廉价且易得的起始物质和易于处理的试剂的情况下，通过短步骤具有经济性、高效性和适用于工业的优点。本发明涉及一种生产光学活性3-羟基-γ-丁内酯的工艺，该化合物由式I表示：其中符号*表示不对称碳原子，包括在异质催化剂和酸性物质的存在下，对式II所表示的光学活性4-取代氧基-3-羟基丁酸酯进行氢化反应，其中R1表示C1-4低级烷基，R2表示羟基保护基，在脱氢氢化反应后解除保护基并同时进行环闭合。