2,3,4-三-O-乙酰基-beta-L-吡喃岩藻糖基叠氮化物 | 95581-07-0

• 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: 2,3,4-三-O-乙酰基-beta-L-吡喃岩藻糖基叠氮化物
• 英文名称: 2,3,4-tri-O-acetyl-β-L-fucopyranosyl azide
• 英文别名: beta-l-Galactopyranosyl azide, 6-deoxy-2,3,4-triacetate；[(2S,3R,4R,5S,6S)-4,5-diacetyloxy-6-azido-2-methyloxan-3-yl] acetate
• CAS: 95581-07-0
• 化学式: C₁₂H₁₇N₃O₇
• 分子量: 315.283
• InChiKey: MKZJGETUNXHZRX-MOBXTKCLSA-N

物化性质

• 熔点：
  125°C
• 沸点：
  454.84°C (rough estimate)
• 密度：
  1.3266 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 海关编码：
  2932999099

SDS

Name:	2 3 4-Tri-O-Acetyl-Beta-L-Fucopyranosyl Azide 99% Material Safety Data Sheet
Synonym:	2,3,4-Tri-O-Acetyl-6-Deoxy-Beta-L-Galactopyranosyl Azide
CAS:	95581-07-0

Section 1 - Chemical Product MSDS Name:2 3 4-Tri-O-Acetyl-Beta-L-Fucopyranosyl Azide 99% Material Safety Data Sheet
Synonym:2,3,4-Tri-O-Acetyl-6-Deoxy-Beta-L-Galactopyranosyl Azide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
95581-07-0	2,3,4-Tri-O-Acetyl-Beta-L-Fucopyranosy	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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant 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 contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light.
Storage:
Keep container closed when not in use. 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# 95581-07-0: 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 and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 124.00 - 126.00 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: C12H17N3O7
Molecular Weight: 315.27

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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:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 95581-07-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3,4-Tri-O-Acetyl-Beta-L-Fucopyranosyl 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# 95581-07-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 95581-07-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 95581-07-0 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：

  2,3,4-三-O-乙酰基-beta-L-吡喃岩藻糖基叠氮化物 在 甲醇 、 copper(ll) sulfate pentahydrate 、 sodium methylate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.25h， 生成 N-(4-(4-{3-[1-(β-L-fucopyranosyl)-1H-1,2,3-triazol-4-yl]phenyl}-1H-1,2,3-triazol-1-yl)phenyl)-3-(pyrrolidin-1-yl)propanamide
  参考文献：
  名称：

  对称和不对称的碳水化合物-苯基二三唑衍生物，作为DNA G-四链体配体：合成，生物物理研究和抗增殖活性。

  摘要：

  在这里，我们介绍了一种基于碳水化合物和苯基吡咯烷基侧链修饰的苯基二三唑（PDTZ）中心核的化合物的新型G4结合家族。通过控制点击化学条件获得它们的合成，可以通过优化的方法获得对称和不对称的carb-PDTZ衍生物，而无需任何中间保护步骤。使用不同的生物物理技术检查了新的carb-PDTZ与各种G-四链体基序的结合。对称的carb-PDTZ衍生物不能稳定G4，但不对称的衍生物（含有一个糖和一个苯基吡咯烷基侧链）则可以稳定G4。有趣的是，不对称carb-PDTZ衍生物相对于双链DNA选择性显示出比对照化合物PDTZ 1高得多的G4选择性，它包含两个苯基吡咯二亚烷基侧链，不含碳水化合物。还通过对不同癌细胞系的体外细胞毒性测量研究了它们潜在的抗肿瘤活性。所有的carb-PDTZ衍生物均显示出比对照PDTZ 1高的IC50值，这可能是由于某些衍生物缺乏化合物稳定性以及较低的细胞摄取所致。

  DOI：

  10.1016/j.bioorg.2020.103786
• 作为产物：
  描述：

  L(-)岩藻糖 在 叠氮基三甲基硅烷 、 silver perchlorate 、 四氯化锡 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 3.0h， 生成 2,3,4-三-O-乙酰基-beta-L-吡喃岩藻糖基叠氮化物
  参考文献：
  名称：

  糖寡酰胺：DNA小沟结合剂的合成

  摘要：

  糖寡酰胺已被设计和合成为结构简单的基于碳水化合物的配体，用于研究碳水化合物与小沟之间的DNA相互作用。在这里，我们报告了一种有效的溶液相合成策略，以获得两个广泛的糖寡酰胺家族。第一种，结构载体A（-Py [Me]-γ-Py-Ind），具有作为取代基存在于吡咯B的氮上的甲基，其连接至寡酰胺片段的C端。第二类，结构向量B（-Py [（CH 2）11OH]-γ-Py-Ind），在吡咯B的氮原子上存在一个烷基链，连接至寡酰胺片段的C末端，并且设计成可接触二价和多价的糖寡酰胺。通过使用顺序的DIPC / HOBt偶联反应，已构建了寡酰胺片段-Py [R]-γ-Py-Ind。端基氨基糖和寡酰胺片段之间的最后偶联反应是通过活化酸衍生物作为BtO-酯来进行的，这是使用TFFH进行的。使用DMF中的DIEA将分离的酯（BtO-Py [R]-γ-Py-Ind）与选定的氨基糖偶联。合成两种不同的选择性模型载体（

  DOI：

  10.1021/jo302238u

文献信息

• Synthesis of biurets <i>via</i> TMSNCO addition to 1-aminosugars: application in the <i>de novo</i> synthesis of dC oxidation products
  作者：Veronika Tsoulougian、Emmanuel E. Psykarakis、Thanasis Gimisis

  DOI：10.1039/c8ob02810a

  日期：——

  and trimethylisocyanate (TMSNCO) was optimised as a one-step synthetic strategy for the synthesis of sugar biurets. This protocol was successfully applied to a number of 1-aminosugars, which exclusively provided the corresponding biurets in 67–99% yields. The new methodology was applied in the de novo synthesis of N1-(2-deoxy-α/β-D-erythro-pentofuranosyl)biuret (dfBU) and N1-(2-deoxy-α/β-D-erythro

  1-氨基糖和三甲基异氰酸酯（TMSNCO）之间的反应被优化为一步合成糖缩二脲的合成策略。该方案已成功应用于多种1-氨基糖，它们以67-99％的产率专门提供了相应的缩二脲。新方法是在所施加的从头合成的Ñ 1 - （2-脱氧- α/β- d -赤-pentofuranosyl）缩二脲（dfBU）和Ñ 1 - （2-脱氧- α/β- d -赤-戊吡喃糖基）缩二脲（dpBU），两个已知的DNA损伤是由羟自由基引起的2'-脱氧胞苷（dCyd）分解引起的。
• Synthesis of glycosyl phosphates and azides
  作者：Subramaniam Sabesan、Susana Neira

  DOI：10.1016/0008-6215(92)80015-s

  日期：1992.1

  -rhamnose and d -mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide to give the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids.

  摘要利用氯代磷酸二苯酯和4-N，N-二甲基氨基吡啶，由邻烷基和酰基化的六吡喃糖制备了富含阴离子的二苯基六吡喃糖基磷酸三酯。通过该方法获得了d-葡萄糖-，d-半乳糖，d-甘露糖，2-乙酰氨基-2-脱氧-d-葡萄糖-，1-fuco-和1-rhamno-吡喃糖基衍生物的糖基磷酸三酯。在0℃以上的温度下，在热力学控制下，主要形成顺式为吡喃糖基C-2-取代基的二苯基糖基磷酸酯，而在低温和动力学控制下，获得具有1,2-反式立体化学的糖基磷酸酯三酯。d-葡萄糖和d-半乳糖衍生物的β-糖基磷酸三酯不稳定，并且会发生异构化为α-糖基磷酸三酯，与1-鼠李糖和d-甘露糖的稳定的β-磷酸酯衍生物相反。这些磷酸三酯已脱保护成糖基磷酸三乙铵盐，适用于制备其他关键的生物衍生物，如核苷酸糖。另外，在异头异构体中心的磷酸二苯酯基团已经被叠氮化物置换，以得到糖基叠氮化物，糖基叠氮化物是糖基氨基酸合成中的关键中间体。
• 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
• OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE CONSTRUCT USING THE SAME, AND METHODS FOR PRODUCING THEM
  申请人：GIFU UNIVERSITY

  公开号：US20180094017A1

  公开（公告）日：2018-04-05

  The oligonucleotide derivative of the present invention is represented by Formula (1). This derivative is considered to be introduced into cells by binding of its amino sugar chain moiety to a ligand on cell surfaces, and have selective drug delivery function. The oligonucleotide derivative can be easily synthesized and introduced into cells without using a lipofection reagent. wherein—A and B are independently modified or unmodified oligonucleotides whose total chain length is 3 or more, and A and B do not contain hydroxyl groups at 3′ and 5′ ends of the oligonucleotide; S represents a sugar substituent, a peptide chain, or a tocopherol-binding group; and an alkyl group may be bound instead of hydrogen bound to a benzene ring.

  本发明的寡核苷酸衍生物由式（1）表示。该衍生物被认为通过其氨基糖链部分与细胞表面的配体结合而被引入细胞，并具有选择性药物传递功能。该寡核苷酸衍生物可以在不使用脂质体载体的情况下轻松合成并引入细胞。其中，A和B分别是经修饰或未经修饰的寡核苷酸，其总链长为3或更长，且A和B不含有寡核苷酸的3′和5′末端的羟基；S代表糖取代基、肽链或生育酚结合基；和烷基基团可以与苯环上的氢结合而不是氢结合。
• AuBr₃-catalyzed azidation of per-<i>O</i>-acetylated and per-<i>O</i>-benzoylated sugars
  作者：Jayashree Rajput、Srinivas Hotha、Madhuri Vangala

  DOI：10.3762/bjoc.14.56

  日期：——

  Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr₃ in good to excellent yields. The method is applicable to a wide range of easily accessible per-O-acetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1–3 h at room temperature, the per-O-benzoylated disaccharides needed 2–3 h of heating at 55 °C.

  在这里，我们首次报道了对经过O-乙酰化和O-苯甲酰化的糖进行顺式异构体化合成的成功实例，通过使用催化量的亲氧化金Br₃，产率良好至优良。该方法适用于广泛易得的O-乙酰化和O-苯甲酰化糖。虽然与O-乙酰化和O-苯甲酰化的单糖在室温下1-3小时内反应完成，但O-苯甲酰化的二糖需要在55°C下加热2-3小时。