七-O-乙酰基-beta-麦芽糖基叠氮化物 | 33012-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 七-O-乙酰基-beta-麦芽糖基叠氮化物
• 中文别名: 2,3,6,2',3',4',6'-七-O-乙酰基-B-D-纤维二糖基叠氮化物
• 英文名称: 2,2',3,3',4',6,6'-hepta-O-acetyl-β-D-cellobiosyl azide
• 英文别名: hepta-O-acetyl-β-D-cellobiosyl azide；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-azido-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 33012-50-9
• 化学式: C₂₆H₃₅N₃O₁₇
• 分子量: 661.574
• InChiKey: JFCQZWVIHHPJTD-SVRUBWSYSA-N

物化性质

• 熔点：
  175°C
• 沸点：
  683.42°C (rough estimate)
• 密度：
  1.4822 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  226
• 氢给体数：
  0
• 氢受体数：
  19

SDS

Name:	Hepta-O-Acetyl-Cellobiosyl-Betha-Azide 99% Material Safety Data Sheet
Synonym:	None known
CAS:	33012-50-9

Section 1 - Chemical Product MSDS Name:Hepta-O-Acetyl-Cellobiosyl-Betha-Azide 99% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
33012-50-9	Hepta-O-Acetyl-Cellobiosyl-Betha-Azide	99	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Light sensitive.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. 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:
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.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. 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 contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from light.

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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# 33012-50-9: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 174.00 - 176.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C26H35N3O17
Molecular Weight: 661.57

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, light, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong 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# 33012-50-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Hepta-O-Acetyl-Cellobiosyl-Betha-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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 33012-50-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 33012-50-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 33012-50-9 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：

  七-O-乙酰基-beta-麦芽糖基叠氮化物 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4-O-BETA-D-吡喃葡萄糖基-BETA-D-吡喃葡萄糖基叠氮化物
  参考文献：
  名称：

  合成吡喃葡萄糖基尿酸叠氮化物的一般方法

  摘要：

  首先将衍生自单糖和二糖的过-O-乙酰化D-甘露聚糖转化为糖基碘，然后与叠氮化物源反应，以在脱乙酰基反应后实现立体选择性合成β-D-糖基叠氮化物。单糖的低温（4摄氏度）TEMPO氧化提供了相应的糖醛酸，其被纯化为游离酸。乳糖基和纤维二糖叠氮化物的氧化导致二酸形成。然而，4'，6'-O-亚苄基保护能够选择性氧化C-6羟基。还制备了2-乙酰胺基-2-脱氧-D-甘露糖基叠氮化物，并将其转化为糖醛酸，从而完成了文库的合成。

  DOI：

  10.1016/s0008-6215(03)00042-9
• 作为产物：
  描述：

  纤维素二糖 在 吡啶 、 sodium azide 、 氢溴酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 七-O-乙酰基-beta-麦芽糖基叠氮化物
  参考文献：
  名称：

  Synthesis of new saccharide azacrown cryptands

  摘要：

  New cryptands including bis-azacrown and saccharidic moieties in their structure were prepared in several steps by applying Staudinger-aza-Wittig reaction (SAW). Syntheses have been started from cheap, easily available commercial compounds such as D-glucose, D-cellobiose and D-lactose subsequently transformed into their derivatives in fairly good yields (60-65%) and suitable to give desired final cryptands by direct SAW coupling reactions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.07.007

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。
• A Generalized Procedure for the One-Pot Preparation of Glycosyl Azides and Thioglycosides Directly from Unprotected Reducing Sugars under Phase-Transfer Reaction Conditions
  作者：Rishi Kumar、Pallavi Tiwari、Prakas R. Maulik、Anup K. Misra

  DOI：10.1002/ejoc.200500646

  日期：2006.1

  Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding

  过氧乙酰化糖基叠氮化物和硫代糖苷直接从未保护的还原糖通过通用的一锅法在相转移条件下原位生成过氧乙酰化糖基溴化物，以优异的收率制备。在糖基溴化物的异头中心完全反转形成立体选择性产物，为制备 1,2-反式糖基叠氮化物和硫代糖苷提供了一种通用的高产率方法。（© Wiley-VCH Verlag GmbH & Co. KGaA， 69451 德国魏因海姆，2006）
• Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids
  作者：Laiqiang Ying、Jacquelyn Gervay-Hague

  DOI：10.1016/j.carres.2003.10.018

  日期：2004.1

  The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis

  描述了适于固相合成的10种N-（氟-9-基甲氧基羰基）甘露糖基氨基糖醛酸的合成。一般的合成策略包括首先引入受保护的胺，然后对C-6羟基进行TEMPO选择性氧化，得到相应的Fmoc保护的糖氨基酸。胺的掺入可通过游离糖的氨解或糖基叠氮化物的还原来完成。该反应可以以多克级进行，从而提供了访问独特单体单元的途径，以便将来将其并入组合文库合成中。
• Divergent Synthesis of Three Classes of Aryl <i>N</i>-Glycosides by Solvent Control
  作者：Jianjun Zhang、Cheng-Wei Tom Chang

  DOI：10.1021/jo8020133

  日期：2009.1.16

  Aryl glycosides represent a group of molecules with immense biological applications and implications. While the syntheses of aryl C-glycosides and O-glycosides have been studied extensively, the preparation for aryl N-glycosides is relatively unexplored. By employing 1,4-naphthoquinone and glycosyl azides undergoing a [3 + 2] cycloaddition, we have developed a convenient method for constructing three

  芳基糖苷代表了一组具有巨大生物学应用和意义的分子。虽然已经广泛研究了芳基C-糖苷和O-糖苷的合成，但是相对未开发芳基N-糖苷的制备方法。通过使用经历[3 + 2]环加成反应的1,4-萘醌和糖基叠氮化物，我们开发了一种便捷的方法来构建包括N在内的三类不同的芳基N-糖苷-通过溶剂控制将糖基化的2-氨基亚甲基-1,3-茚满二酮，苯并ze庚因-1,5-二酮和9,10-蒽醌衍生物。发现在DMF中进行环加成仅形成9,10-蒽醌衍生物，而极性较小的溶剂如甲苯提供所有三个芳基N-糖苷。N-糖基化的9，10-蒽醌衍生物的合成是特别令人感兴趣的，因为没有已知的例子被记录。这些氮的合成使用传统糖基化方法的β-糖基化杂环化合物可能具有挑战性。因此，我们面向多样性的协议可以看作是一种替代性的实用糖基化方法。另外，我们还证明了烷基叠氮化物也可以经历相同的环加成，进一步扩大了可用于更广泛兴趣的结构库。最初的抗癌检测表明19f和19k分别产生17
• Synthesis of Sugar-Derived Triazole- and Pyridine-Based Metal Complex Ligands
  作者：Thomas Ziegler、Jochen Kraft、Daniel Schmollinger、Jakob Maudrich

  DOI：10.1055/s-0034-1379473

  日期：——

  for metals were prepared by copper-catalyzed coupling (CLICK reaction) of 2-ethynylpridine, 2-ethynyl-5-nitropyridine, 2-ethynylquinoline, and 2,6-diethynylpyridine with 12 protected glycosyl azides in the gluco and galacto series and 2 benzyl azides. The 1,2,3-triazole-linked glycoconjugates prepared were used as ligands for the copper-catalyzed addition of phenylacetylene to N-benzylideneaniline to

  摘要 通过2-乙炔基吡啶，2-乙炔基-5-硝基吡啶，2-乙炔基喹啉和2,6-二乙炔吡啶与十二种保护的糖基叠氮化物的铜催化偶联（CLICK反应），制备了一系列30种金属的双齿和三齿配体在葡萄糖和半乳糖系列中和2个苄基叠氮化物。制备的1,2,3-三唑连接的糖缀合物用作配体，用于铜催化的苯乙炔加成到N-亚苄基苯胺上，得到手性N-（1,3-二苯基丙-2-炔-1-基）苯胺。 通过2-乙炔基吡啶，2-乙炔基-5-硝基吡啶，2-乙炔基喹啉和2,6-二乙炔吡啶与十二种保护的糖基叠氮化物的铜催化偶联（CLICK反应），制备了一系列30种金属的双齿和三齿配体在葡萄糖和半乳糖系列中和2个苄基叠氮化物。制备的1,2,3-三唑连接的糖缀合物用作配体，用于铜催化的苯乙炔加成到N-亚苄基苯胺上，得到手性N-（1,3-二苯基丙-2-炔-1-基）苯胺。