3,4-二-乙酰基-D-木糖烯 | 3152-43-0

• 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: 3,4-二-乙酰基-D-木糖烯
• 英文名称: 3,4-di-O-acetyl-D-xylal
• 英文别名: di-O-acetyl-D-xylal；3,4-di-O-acetyl-1,5-anhydro-2-deoxy-d-threo-pent-1-enitol；(3R,4R)-3,4-dihydro-2H-pyran-3,4-diyl diacetate；[(3R,4R)-4-acetyloxy-3,4-dihydro-2H-pyran-3-yl] acetate
• CAS: 3152-43-0
• 化学式: C₉H₁₂O₅
• 分子量: 200.191
• InChiKey: OWKCFBYWQGPLSJ-RKDXNWHRSA-N

物化性质

• 熔点：
  40-42 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  266.2±40.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25

SDS

Name:	3,4-Di-O-acetyl-D-xylal Material Safety Data Sheet
Synonym:
CAS:	3152-43-0

Section 1 - Chemical Product MSDS Name: 3,4-Di-O-acetyl-D-xylal Material Safety Data Sheet
Synonym:

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3152-43-0	3,4-Di-O-acetyl-D-xylal		unlisted

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

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Not available. 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. May be harmful if swallowed.
Inhalation:
May cause 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. Vacuum or sweep up material and place into a suitable disposal 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:
Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 3152-43-0: 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: Solid or liquid
Color: Not available.
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: C9H12O5
Molecular Weight: 200.19

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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# 3152-43-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Di-O-acetyl-D-xylal - 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 Not regulated as a hazardous material. IMO Not regulated as a hazardous material. 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# 3152-43-0: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 3152-43-0 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 3152-43-0 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 6/10/2003 Revision #0 Date: Original. The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,4-二-乙酰基-D-木糖烯 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 di-O-benzoyl-L-arabinal
  参考文献：
  名称：

  有机锌试剂高度立体选择性地添加到戊吡喃糖衍生的糖中：保护基团的作用和C-糖苷立体化学的赋值

  摘要：

  将3-丙酰碘化乙基乙酯亲核加成到各种受不同保护的戊吡喃糖衍生的d-糖6a - g上，具有很好的非对映选择性，提供了相应的β- C-糖苷7。所述的立体化学对-nitrobenzoate衍生物7D已通过X射线晶体学确认，其它β-的立体化学Ç糖苷产品已关联到7d的。观察到的立体化学结果支持了Isobe的早期建议，即通空效应对于稳定和控制11代表的中间氧鎓物种的反应性很重要。

  DOI：

  10.1016/j.tet.2004.04.004
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 氢溴酸 、 氯化铵 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.25h， 生成 3,4-二-乙酰基-D-木糖烯
  参考文献：
  名称：

  从甘醇异头物高度非对映选择性合成 C-糖苷

  摘要：

  这封信介绍了使用手性N -杂环卡宾 - 铜催化剂从甘醇异头物高度非对映选择性合成C -羟基次甲基糖苷。高非对映选择性受底物的立体中心和N-杂环卡宾-铜配合物的手性协同控制，而不会被 C5 的立体化学和端基异构位置打断。这种方法能够使用合成通用的糖醛和各种功能化的醛来生产各种C-羟基次甲基糖苷。

  DOI：

  10.1021/acs.orglett.3c01605

文献信息

• Synthesis of xylal‐ and arabinal‐based crown ethers and their application as asymmetric phase transfer catalysts
  作者：Tamás Nemcsok、Zsolt Rapi、Péter Bagi、György Keglevich、Péter Bakó

  DOI：10.1002/chir.23149

  日期：2020.1

  from l‐ and d‐xylose, and l‐ and d‐arabinose, respectively. These monosaccharide‐based chiral macrocycles were tested as phase transfer catalysts in a few asymmetric reactions. The xylal‐based crown compounds proved to be efficient catalysts in a few liquid‐liquid phase reactions. The epoxidation of trans‐chalcone and the Darzens condensation of α‐chloroacetophenone with benzaldehyde took place with

  基于arabinal新xylal-和单氮杂-15-冠醚5合成从开始升-和ð木糖，和升和- d分别-arabinose。这些基于单糖的手性大环化合物在一些不对称反应中作为相转移催化剂进行了测试。在一些液相-液相反应中，基于木糖的冠状化合物被证明是有效的催化剂。反式的环氧化α-氯苯乙酮与苯甲醛的查尔酮和达岑（Darzens）缩合反应具有完全非对映选择性，分别高达ee的77％和ee的58％。发现查尔酮和α-氯乙酰苯的芳香环中的取代基对对映选择性有影响。最高的ee值来自4-氯查尔酮的环氧化（81％ee）和2-萘基类似物的反应（96％ee），而4-苯基-α-氯乙酰苯与苯甲醛的Darzens缩合反应，检测到的最大ee为91％。冠环中单糖单元的构型影响合成的环氧酮的绝对构型。
• Ruthenium catalyzed synthesis of 2,3-unsaturated C-glycosides from glycals
  作者：Batthula Srinivas、Thurpu Raghavender Reddy、Sudhir Kashyap

  DOI：10.1016/j.carres.2015.01.009

  日期：2015.4

  for the synthesis of 2,3-unsaturated C-glycosides. Various nucleophiles such as allyl trimethylsilane, triethylsilane, trimethylsilyl cyanide, trimethylsilyl azide and heterocycles such as thiophene and furan reacted smoothly with glycals in the presence of catalytic amount of ruthenium trichloride under mild reaction conditions.

  使用氯化钌（III）开发了一种高效且便捷的C-糖基化方法，用于合成2,3-不饱和C-糖苷。在温和的反应条件下，在催化量的三氯化钌存在下，各种亲核试剂（如烯丙基三甲基硅烷，三乙基硅烷，三甲基甲硅烷基氰化物，三甲基甲硅烷基叠氮化物）和杂环（如噻吩和呋喃）与糖类平稳地反应。
• Preparation of acylated pyranoid glycals in neutral aqueous medium by using chromium(II) complexes as reagents
  作者：Gyöngyvér Kovács、Krisztina Tóth、Zoltán Dinya、László Somsák、Károly Micskei

  DOI：10.1016/s0040-4020(99)00170-2

  日期：1999.4

  gave (13) in 70–90% yields and >95% purity. Complexes of Cr(II) with L = EDTA, NTA were similarly efficient with chloride (2) in furnishing glucal 13, while with L = IDA, GLY, MAL hydrolysis of 2 could not be suppressed. Under the same conditions [CrII(EDTA)]2− also efficiently gave the corresponding glycals 14–19 from and bromide (5), per-O-acetylated α-d-galactopyranosyl chloride (6) and bromide (7)

  的反应溴化物（3）用铬（II）L-络合物（L = EDTA，NTA，IDA，GLY，MAL）在中性（5 95纯度％。Cr（II）与L = EDTA，NTA的配合物与氯化物（2）在提供葡聚糖13方面同样有效，而L = IDA，GLY则无法抑制2的MAL水解。在相同条件下[CR II（EDTA）] 2-也有效地得到相应的烯糖14-19从和溴化物（5），per- Ô -acetylatedα-d吡喃半乳糖基氯化物（6）和溴化物（7），α-d-吡喃吡喃糖基氯（8），α-d-吡喃吡喃糖基氯（9）和溴化物（10），β-​​d-阿拉伯吡喃糖基溴化物（11）和α-1-鼠李糖基吡喃糖基氯化物（12）。
• A mild and efficient Zn-catalyzed C-glycosylation: synthesis of C(2)–C(3) unsaturated C-linked glycopyranosides
  作者：Thurpu Raghavender Reddy、Dodla Sivanageswara Rao、Sudhir Kashyap

  DOI：10.1039/c5ra03328d

  日期：——

  A mild and efficient protocol for theC-glycosylation from glycals is described by using Zn-catalysis.

  使用锌催化剂描述了一种从糖醛中进行C-糖基化的温和高效的方法。
• The use of ultrastable Y zeolites in the Ferrier rearrangement of acetylated and benzylated glycals
  作者：Pieter Levecque、David W. Gammon、Pierre Jacobs、Dirk De Vos、Bert Sels

  DOI：10.1039/b921051b

  日期：——

  The Ferrier rearrangement of a selection of protected glycals was successfully performed using a commercially available H-USY zeolite CBV-720 as catalyst, selected after screening a range of similar catalysts. By incorporating either alcohols, thiophenol, trimethylsilyl azide or allyltrimethylsilane in the reaction it was shown that a range of O-, S-, N- and C-glycosides could be formed. With benzylated glucal and galactal in particular, use of the CBV-720 catalyst led to significantly higher yields of the 2,3-dehydroglycosides than previously reported.

  使用商业可获得的H-USY沸石CBV-720作为催化剂，对一系列保护性甘露糖环进行Ferrier重排反应，该催化剂是在筛选了一系列类似的催化剂后选出的。通过在反应中加入醇、硫酚、三甲基甲硅烷基叠氮化物或烯丙基三甲基硅烷，证明了可以形成一系列O-、S-、N-和C-糖苷。特别是对于苄基化的葡萄糖醇和半乳糖醇，使用CBV-720催化剂可以获得比先前报道的2,3-脱氢糖苷的产量明显更高的产率。