1-azido-1-deoxy-β-D-glucopyranoside tetraacetate | 13992-25-1

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate
• 英文别名: 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl azide；tetra-O-acetyl-β-D-glucopyranosyl azide；(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate；1-azido-1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose；1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)azide；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-azidooxan-2-yl]methyl acetate
• CAS: 13992-25-1
• 化学式: C₁₄H₁₉N₃O₉
• 分子量: 373.32
• InChiKey: NHNYHKRWHCWHAJ-RKQHYHRCSA-N

物化性质

• 熔点：
  127-131 °C(lit.)
• 沸点：
  502.57°C (rough estimate)
• 密度：
  1.3271 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R2
• WGK Germany：
  3
• 海关编码：
  29329990
• 危险品运输编号：
  1325
• 储存条件：
  2-8℃

SDS

Name:	2 3 4 6-Tetra-o-acetyl-betha-d-glucopyranosyl azide 98% Material Safety Data Sheet
Synonym:
CAS:	13992-25-1

Section 1 - Chemical Product MSDS Name:2 3 4 6-Tetra-o-acetyl-betha-d-glucopyranosyl azide 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13992-25-1	2,3,4,6-TETRA-O-ACETYL-BETHA-D-GLUCOPY	98%	unlisted

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.Light sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid.
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:

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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:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. 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.
Keep under a nitrogen blanket.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 13992-25-1: 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: Solid
Color: beige
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 129 - 130 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: C14H19N3O9
Molecular Weight: 373.32

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13992-25-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3,4,6-TETRA-O-ACETYL-BETHA-D-GLUCOPYRANOSYL AZIDE - 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# 13992-25-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13992-25-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13992-25-1 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

制备方法与用途

2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖叠氮化物是一种生物化学试剂，可用作生物材料或有机化合物，广泛应用于生命科学的相关研究中。

反应信息

• 作为反应物：
  描述：

  1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 甲醇 、 氨 、 镍 、 乙酸乙酯 作用下， 生成 N-benzyl-D-glucopyranosylamine
  参考文献：
  名称：

  Helferich; Mitrowski, Chemische Berichte, 1952, vol. 85, p. 1,7

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 叠氮基三甲基硅烷 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到1-azido-1-deoxy-β-D-glucopyranoside tetraacetate
  参考文献：
  名称：

  Synthesis of acylated glycoconjugates as templates to investigate in vitro biopharmaceutical properties

  摘要：

  A series of novel glycopyranosyl azides were synthesised wherein the carbohydrate moiety was peracylated with four acetyl, propionyl, butanoyl, pentanoyl (valeryl) or 3-methylbutanoyl (isovaleryl) ester linked groups. A panel of glycoconjugates was synthesised from these glycopyranosyl azides using copper-catalysed azide-alkyne cycloaddition. The in vitro metabolic stability, plasma stability and plasma protein binding was then measured to establish the impact of the different acyl group when presented on a common scaffold. The acetyl, propionyl and butanoyl esters exhibited metabolism consistent with esterase processing, and various mono-, di- and tri-acylated hydrolysis products as well as the fully hydrolysed compound were detected. In contrast, the pentanoyl and 3-methylbutanoyl esters were stable. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.056

文献信息

• Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations
  作者：Laura Sršan、Thomas Ziegler

  DOI：10.3762/bjoc.16.80

  日期：——

  disaccharides containing glycopeptides were prepared in solution. The applicability of two common peptide coupling reagents, using an orthogonal Fmoc/t-Bu strategy along with acetyl protecting groups for the carbohydrate moiety, was studied. Thus, the prepared libraries of glycopeptides were designed as model systems of cell surfaces for future investigations by combined preparative mass spectroscopy and

  为了研究寡糖和拟肽的生物学功能，在溶液中制备了新的含有糖肽的天冬酰胺基单糖和二糖。使用正交的Fmoc / t- Bu策略以及碳水化合物部分的乙酰基保护基，研究了两种常见的肽偶联剂的适用性。因此，将制备的糖肽文库设计为细胞表面的模型系统，以供将来通过在金属表面上使用软着陆电喷雾束沉积（ES-IBD）的组合制备质谱和扫描隧道显微镜（STM）进行研究。
• Stereospecific Synthesis of the α- and β-<scp>d</scp>-Glucopyranosyl Ureas
  作者：Yoshiyasu Ichikawa、Taihei Nishiyama、Minoru Isobe

  DOI：10.1021/jo0100751

  日期：2001.6.1

  A new, one-pot, two-stage procedure for the preparation of the alpha- and beta-D-glucopyranosyl ureas has been developed. Oxidation of glucopyranosyl isocyanides provides glucopyranosyl isocyanates, which can be trapped in situ with amines to afford good yields of glucopyranosyl ureas. Application of this method establishes the successful synthesis of the hitherto unknown N,N'-di-alpha,alpha- and alpha

  已经开发了一种新的，一锅，两阶段的制备α-和β-D-吡喃葡萄糖基脲的方法。吡喃葡萄糖基异氰酸酯的氧化提供了吡喃葡萄糖基异氰酸酯，其可以用胺原位捕获以提供良好产率的吡喃葡萄糖基脲。该方法的应用建立了迄今为止未知的N，N′-二-α，α-和α，β-D-吡喃葡萄糖基脲的成功合成。
• Copper-Catalyzed Huisgen and Oxidative Huisgen Coupling Reactions Controlled by Polysiloxane-Supported Amines (AFPs) for the Divergent Synthesis of Triazoles and Bistriazoles
  作者：Zhan-Jiang Zheng、Fei Ye、Long-Sheng Zheng、Ke-Fang Yang、Guo-Qiao Lai、Li-Wen Xu

  DOI：10.1002/chem.201202472

  日期：2012.10.29

  click reactions mediated by a polysiloxane‐supported secondary amine allow the preparation of novel heterocyclic compounds, that is, bistriazoles. Comparably, it is also surprising that the use of a diamine‐functional polysiloxane as ligand led to a classic Huisgen [3+2] cycloaddition in excellent yields. From the results of the present amine‐functional polysiloxanes‐controlled Huisgen reaction or oxidative

  在点击化学中成功地提出了一个有趣的例子，该例子采用铜（I）和胺官能大分子聚硅氧烷体系发散催化。在本手稿中，我们证明了仲胺官能聚硅氧烷在叠氮化物和炔烃的铜介导的惠斯根反应中诱导氧化偶联的显着能力，从而获得了良好的收率和选择性。由聚硅氧烷负载的仲胺介导的点击反应可制备新型杂环化合物，即双三唑。相比之下，使用二胺官能化聚硅氧烷作为配体也导致了经典的Huisgen [3 + 2]环加成反应，且收率很高，这也令人惊讶。
• First noscapine glycoconjugates inspired by click chemistry
  作者：Kunj B. Mishra、Ram C. Mishra、Vinod K. Tiwari

  DOI：10.1039/c5ra07321a

  日期：——

  A number of novel 7-O-noscapine glycoconjugates have been synthesized starting from noscapine, an alkaloid found in the opium plant, via two successive steps. The first step is a selective 7-O-demethylation of noscapine and the next is a subsequent propargylation which affords 7-O-propargyl noscapine (3) in good yield. The structure was confirmed by extensive spectroscopic data including single crystal

  已经通过两个连续的步骤，从鸦片植物中发现的一种生物碱-诺斯卡汀开始合成了许多新颖的7- O-诺斯卡汀糖缀合物。第一步是Noscapine的选择性7- O-去甲基化，第二步是随后的炔丙基化，以良好的收率得到7- O-炔丙基基Noscapine（3）。通过包括单晶X射线数据在内的大量光谱数据证实了该结构。研究了发达的Noscapine衍生物3与糖基叠氮化物6a–m的1,3-偶极环加成反应，得到了三唑连接的第二代Noscapine类似物，其糖缀合物形式（8a–m ）以增强Noscapine的治疗功效。
• Syntheses and structures of anomeric quaternary ammonium β-glucosides and comments on the anomeric C–N bond lengths
  作者：Lisa Iddon、Ryan A. Bragg、John R. Harding、Chandrakala Pidathala、John Bacsa、Anthony J. Kirby、Andrew V. Stachulski

  DOI：10.1016/j.tet.2009.05.086

  日期：2009.8

  We report convenient syntheses of anomeric quaternary ammonium β-glucosides in both protected and deprotected forms, together with X-ray structural investigations of two of the products. Both the quaternisation of a protected anomeric N,N-(dimethylamino)glucose, derived in two high-yielding steps from the anomeric azide, and the direct reaction of glucose or 6-O-trityl glucose with a secondary amine

  我们报告了保护和脱保护形式的端粒异构季铵β-葡萄糖苷的方便合成方法，以及两种产品的X射线结构研究。受保护的异头N，N-（二甲基氨基）葡萄糖的季铵化作用，是在两个高产步骤中从异头叠氮化物衍生而来的，并且葡萄糖或6- O-三苯甲基葡萄糖与仲胺直接反应，然后进行保护和季铵化是可行的路线。我们还讨论了在立体电子效应方面观察到的C–N键长和产物稳定性的重要性。