β-D-葡萄糖胺五乙酸酯 | 7772-79-4

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: β-D-葡萄糖胺五乙酸酯
• 中文别名: 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖-1,3,4,6-四乙酸盐；2-乙酰氨基-1,3,4,6-四-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖；D-氨基葡萄糖四醋酸盐；五乙酰基-β-D-葡萄糖胺；2-氨基-2-脱氧-β-D-葡萄糖五乙酸酯；2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖-1,3,4,6-四乙酸；D-氨基葡萄糖五醋酸盐
• 英文名称: 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose
• 英文别名: 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose；N-acetyl-β-D-glucosamine tetraacetate；β-D-glucosamine pentaacetate；N-Acetyl-beta-D-glucosamine tetraacetate；[(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 7772-79-4
• 化学式: C₁₆H₂₃NO₁₀
• 分子量: 389.359
• InChiKey: OVPIZHVSWNOZMN-OXGONZEZSA-N

物化性质

• 熔点：
  186-189 °C(lit.)
• 沸点：
  530.2±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微、加热、超声处理）、甲醇（轻微、加热、超声处理）
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解。请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29329990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  -20℃

SDS

Name:	2-Acetamido-2-Deoxy-1 3 4 6-Tetra-O-Acetyl-beta-D-Glucopyranose Material Safety Data Sheet
Synonym:	beta-D-Glucosamine Pentaacetate
CAS:	7772-79-4

Section 1 - Chemical Product MSDS Name:2-Acetamido-2-Deoxy-1 3 4 6-Tetra-O-Acetyl-beta-D-Glucopyranose Material Safety Data Sheet
Synonym:beta-D-Glucosamine Pentaacetate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
7772-79-4	2-Acetamido-2-Deoxy-1,3,4,6-Tetra-O-Ac	ca. 100	231-865-4

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
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. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam. Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a dry area. Deep freeze (below -20C).

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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# 7772-79-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 186 - 189 deg C
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: C16H23NO10
Molecular Weight: 389.35

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 7772-79-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Acetamido-2-Deoxy-1,3,4,6-Tetra-O-Acetyl-beta-D-Glucopyran - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 7772-79-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 7772-79-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 7772-79-4 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：

  β-D-葡萄糖胺五乙酸酯 在 lipase (Aspergillus niger AP₆ Amano) 作用下， 以 水 、 乙酸乙酯 、 异丙醇 为溶剂， 以93%的产率得到2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  直接与天然N-乙酰基保护基合成N-乙酰基氨基葡萄糖和Gal-β（1-3）GalNAc（T抗原）的α-连接衍生物

  摘要：

  已通过涉及完全立体选择性迈克尔加成的新方法，以1,2-顺式方式将适合于蛋白质载体偶联的α-连接的间隔臂直接引入到GlcNAc和Gal-β（1-3）GalNAc上。将异头醇酸钠加到由丙二醛和甲苯磺酰氯的钠盐就地制备的β-甲苯磺酰丙烯醛上。

  DOI：

  10.1039/c39890001918
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 三氟化硼乙醚 、 氰化汞 、 mercury dibromide 作用下， 以 硝基甲烷 、 甲苯 、 苯 为溶剂， 反应 4.5h， 生成 β-D-葡萄糖胺五乙酸酯
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006

文献信息

• Solid-Phase Synthesis of Di-N-Acetyl-β-Chitobiosyl NAG-Thiazoline
  作者：Gangliang Huang、Ya Chen

  DOI：10.2174/157018011796235220

  日期：2011.8.1

  The solid-phase synthesis of di-N-acetyl-β-chitobiosyl NAG (N-acetyl D-glucosamine)-thiazoline 3 was reported. After the 6-O-benzyl NAG-thiazoline 9, NHCbz trichloroacetimidate donors 14, and 21 were synthesized, and solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β-chitobiosyl NAGthiazoline 3 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

  据报道，进行了双-N-乙酰-β-壳二糖基NAG（N-乙酰-D-葡萄糖胺）噻唑啉3的固相合成。首先合成了6-O-苄基NAG噻唑啉9、NHCbz三氯乙酸亚胺供体14和21，然后使用Wang树脂作为支持体进行固相合成。通过迭代糖基化反应、催化氢化、乙酰化和脱乙酰化，分别获得了目标双-N-乙酰-β-壳二糖基NAG噻唑啉3。
• Galacto, Gluco, Manno<i>,</i> and Disaccharide-Based <i>C-</i>Glycosides of 2-Amino-2-deoxy Sugars
  作者：Laura Grant、Yan Liu、Kenneth E. Walsh、Daryl S. Walter、Timothy Gallagher

  DOI：10.1021/ol0269695

  日期：2002.12.1

  underwent facile C-Se homolysis to provide the corresponding anomeric radicals, which were trapped with alkenes to give C-glycosides. This provides a general entry to alpha-C-glycosides based on 2-amino-2-deoxy sugars that is also applicable to disaccharide variants.

  [反应：见正文]从易得的前体开始，通过一或两个步骤的方法制备衍生自GalNAc，GlcNAc和ManNAc的硒代糖苷。对异头硒化物进行轻松的C-Se均质分解，以提供相应的异头自由基，这些自由基被烯烃捕获，得到C-糖苷。这提供了基于2-氨基-2-脱氧糖的α-C-糖苷的一般入口，其也适用于二糖变体。
• Iminocyclitol inhibitors of hexoaminidase and glycosidase
  申请人：The Scripps Research Institute

  公开号：US06774140B1

  公开（公告）日：2004-08-10

  Designed iminocylitols that have potent inhibition activity with respect to hexominidases and glycosides are disclosed.

  披露了设计的亚氨基糖醇，它们对己糖苷酶和苷具有强大的抑制活性。
• Preparation of aminoethyl glycosides for glycoconjugation
  作者：Robert Šardzík、Gavin T Noble、Martin J Weissenborn、Andrew Martin、Simon J Webb、Sabine L Flitsch

  DOI：10.3762/bjoc.6.81

  日期：——

  The synthesis of a number of aminoethyl glycosides of cell-surface carbohydrates, which are important intermediates for glycoarray synthesis, is described. A set of protocols was developed which provide these intermediates, in a short number of steps, from commercially available starting materials.

  描述了细胞表面碳水化合物的许多氨基乙基糖苷的合成，它们是 glycoarray 合成的重要中间体。开发了一套方案，这些方案可以在很短的步骤中从市售的起始材料中提供这些中间体。
• A Terpyridine Zinc Complex for Selective Detection of Lipid Pyrophosphates: A Model System for Monitoring Bacterial O- and N-Transglycosylations
  作者：Tse-Wei Hsu、Hsin-Chuan Hsu、Hsin-Yu Chan、Jim-Min Fang

  DOI：10.1021/acs.joc.0c01252

  日期：2020.10.2

  To develop an effective method for probing O- and N-glycosyltransfer reactions that are accompanied by the release of undecaprenyl pyrophosphate, solanesyl pyrophosphate (SPP) is used as a surrogate to bind a terpyridine zinc complex (Tpy-Zn), forming a fluorescent [Tpy-Zn]-SPP complex (Kass 106,000 M–1 in EtOH-CHCl3) with 5.8 μM LOD in HEPES buffer (10 mM, pH 7.4) containing 10 mM CaCl2 and 0.08%

  为了开发一种有效的方法来探测伴有十一碳烯基焦磷酸盐释放的O-和N-糖基转移反应，使用茄基焦磷酸盐（SPP）作为替代物来结合一个联吡啶锌配合物（Tpy-Zn），形成一种荧光[ Tpy-Zn] -SPP络合物（EtOH-CHCl 3中的K驴106,000 M –1），在含有10 mM CaCl 2和0.08％癸基PEG的HEPES缓冲液（10 mM，pH 7.4）中具有5.8μMLOD。脂质II聚合的生物测定条件。

表征谱图