(2S,3S,4R)-3,4-二乙酰氧基-3,4-二氢-2H-吡喃-2-羧酸甲酯 | 57690-62-7

• 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: (2S,3S,4R)-3,4-二乙酰氧基-3,4-二氢-2H-吡喃-2-羧酸甲酯
• 英文名称: methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate
• 英文别名: methyl 3,4-di-O-acetyl-D-glucuronal；methyl (2S,3S,4R)-3,4-diacetyloxy-3,4-dihydro-2H-pyran-2-carboxylate
• CAS: 57690-62-7
• 化学式: C₁₁H₁₄O₇
• 分子量: 258.228
• InChiKey: QYYMNOQXLQYOFN-UTLUCORTSA-N

物化性质

• 溶解度：
  可溶于丙酮（少许）、氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 安全说明：
  S24/25

SDS

Name:	Methyl 3 4-di-O-acetyl-D-glucuronal Material Safety Data Sheet
Synonym:
CAS:	57690-62-7

Section 1 - Chemical Product MSDS Name:Methyl 3 4-di-O-acetyl-D-glucuronal Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
57690-62-7	Methyl 3,4-di-O-acetyl-D-glucuronal		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# 57690-62-7: 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: 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: C11H14O7
Molecular Weight: 258.23

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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# 57690-62-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 3,4-di-O-acetyl-D-glucuronal - 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# 57690-62-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 57690-62-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 57690-62-7 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：

  (2S,3S,4R)-3,4-二乙酰氧基-3,4-二氢-2H-吡喃-2-羧酸甲酯 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 以65%的产率得到methyl (1S,3S,4S,5S,6R)-4,5-diacetyloxy-2,7-dioxabicyclo[4.1.0]heptane-3-carboxylate
  参考文献：
  名称：

  WO2008/138389

  摘要：

  公开号：
• 作为产物：
  描述：

  D-GLUCURONIDEMETHYLESTERD-葡糖苷酸甲酯 在 高氯酸 、 氢溴酸 、 锌 作用下， 以 乙酸甲酯 、 水 、 溶剂黄146 为溶剂， 反应 47.0h， 生成 (2S,3S,4R)-3,4-二乙酰氧基-3,4-二氢-2H-吡喃-2-羧酸甲酯
  参考文献：
  名称：

  Fehlhaber, Hans-Wolfram; Snatzke, Guenther; Vlahov, Iontscho, Liebigs Annalen der Chemie, 1987, p. 637 - 638

  摘要：

  DOI：

文献信息

• Improved and large-scale synthesis of different protected d-glucuronals
  作者：Hannes Mikula、Dominik Matscheko、Markus Schwarz、Christian Hametner、Johannes Fröhlich

  DOI：10.1016/j.carres.2013.01.007

  日期：2013.4

  was converted to methyl 3,4-di-O-acetyl-D-glucuronal applying a novel one-pot protocol, which allowed for large-scale synthesis. Introduction of silyl and benzyl groups was achieved using optimized procedures. Furthermore 3,4,6-tri-O-acetyl-D-glucal was used as starting material for an improved preparation of benzyl protected D-glucuronal, which significantly accelerates and simplifies similar methods

  尽管将不同的受保护的D-葡萄糖醛酸用作制备许多化合物的前体，但文献中仍未描述标准方法和大规模合成方法。在开发不同的受保护d-葡萄糖醛酸基供体的过程中，我们开发了几种通用方法，可用于快速，可重复地制备大量关键中间体。应用新型一锅法将D-葡萄糖醛酸内酯转化为甲基3,4-二-O-乙酰基-D-葡萄糖醛酸，可大规模合成。甲硅烷基和苄基的引入是使用优化程序实现的。此外，将3,4,6-三-O-乙酰基-D-葡糖醛用作起始原料，用于改进的苄基保护的D-葡糖醛酸醛的制备，其显着加速并简化了文献中所述的类似方法。
• Amphiphilic poly(sugar amino acid)s: a novel class of glycoclusters for supramolecular materials
  作者：Shin-Ichiro Nishimura

  DOI：10.1039/a708555i

  日期：——

  A poly(sugar amino acid) having self-assembling properties was efficiently synthesised by simple polymerisation of 1-O-dodecyl-2-amino-2-deoxy-β-D-glucopyranosiduronic acid 7 derived from D-glucofuranurono-6,3-lactone as the key starting material.

  通过简单聚合1-O-十二烷基-2-氨基-2-脱氧-β-D-吡喃葡糖醛酸7（以D-葡呋喃糖醛酸-6,3-内酯为关键起始原料），高效地合成了一种具有自组装特性的聚（糖氨基酸）。
• Palladium-Catalyzed Oxidative Synthesis of Highly Functionalized Ortholactones
  作者：Kate L. Baddeley、Qun Cao、Mark J. Muldoon、Matthew J. Cook

  DOI：10.1002/chem.201500862

  日期：2015.5.18

  A palladium‐catalyzed oxidative reaction is reported which converts dihydropyrans to their corresponding ortholactone. The products are formed in good to excellent yields with a very high level of chemoselectivity and functional group tolerance. Mechanistic studies confirm that the reaction proceeds by a Wacker‐type mechanism.

  据报道，钯催化的氧化反应会将二氢吡喃转化为相应的原内酯。形成的产品产率高到优，具有很高的化学选择性和官能团耐受性。机理研究证实，反应是通过Wacker型机理进行的。
• The First Synthesis of Herbicidin B. Stereoselective Construction of the Tricyclic Undecose Moiety by a Conformational Restriction Strategy Using Steric Repulsion between Adjacent Bulky Silyl Protecting Groups on a Pyranose Ring
  作者：Satoshi Ichikawa、Satoshi Shuto、Akira Matsuda

  DOI：10.1021/ja992608h

  日期：1999.11.1

  The first total synthesis of the nucleoside antibiotic herbicidin B (1b) was achieved, where a novel aldol-type C-glycosidation reaction promoted by samarium diiodide (SmI2) was used as a key step. Treatment of methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-d-glucuronate (13) with SmI2 in THF regioselectively gave the corresponding 1-enolate, which was readily trapped

  实现了核苷类抗生素除草素 B (1b) 的首次全合成，其中以二碘化钐 (SmI2) 促进的新型羟醛型 C-糖苷化反应为关键步骤。在 THF 中用 SmI2 处理 3,4-O-(1,1,3,3-四异丙基-1,3-二硅氧烷二基)-1-苯硫基-2-ulos-β-d-葡萄糖醛酸甲酯 (13) 区域选择性地得到相应的 1-烯醇化物，它很容易被 1-β-d-木糖基腺嘌呤 5'-醛衍生物 7 捕获，得到产物 19a，b，为异头混合物。使用 Burgess 内盐对 19a,b 中的 5'-羟基进行脱水得到烯酮 20，随后将其氢化得到十一碳呋喃酮基腺嘌呤衍生物 21。21 的脱保护得到三环糖核苷 23。然而，它是6' 位的除草剂 B。通过使用基于吡喃糖环上相邻大保护基团之间排斥的构象限制策略来构建所需的 6'-α-构型。因此，当甲基 3-O-叔...
• Unusual Reactions of Enopyranuronates with Hydroxy Acid Esters under Ferrier Conditions
  作者：Eusebius Wieczorek、Joachim Thiem

  DOI：10.1055/s-1998-1697

  日期：1998.5

  Instead of typical allylic rearrangement product formation the reactions of glucuronal with various hydroxy acid esters under Ferrier conditions led to 1,3-disubstituted derivatives.

  在 Ferrier 条件下，葡萄糖醛酸与各种羟基酸酯的反应生成了 1,3-二取代衍生物，而不是典型的烯丙基重排产物。