beta-D-吡喃葡萄糖胺 | 7284-37-9

• 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: beta-D-吡喃葡萄糖胺
• 英文名称: D-glucopyranosyl amine
• 英文别名: β-D-glucopyranosylamine；β-D-glucosylamine；beta-D-Glucopyranosylamine；(2R,3R,4S,5S,6R)-2-amino-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 7284-37-9
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: WCWOEQFAYSXBRK-VFUOTHLCSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  416.4±45.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于酸性水溶液（轻微）、甲醇（轻微）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  -20°C，避光，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Beta-d-glucopyranosylamine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Beta-d-glucopyranosylamine
CAS number: 7284-37-9

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H13NO5
Molecular weight: 179.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  beta-D-吡喃葡萄糖胺 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 2.5h， 生成 N-(β-D-glucopyranosyl)-N²-acetyl-S-nitroso-D-penicillamine amide
  参考文献：
  名称：

  Glyco-S-nitrosothiols, a novel class of no donor compounds

  摘要：

  Three novel glyco-S-nitrosothiol NO donor compounds 1, 2, and 3 have been synthesized. These compounds outperform S-nitroso-N-acetylpenicillamine (SNAP) in aqueous solubility and stability, with and without EDTA and in the presence or absence of Cu2+. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00484-2
• 作为产物：
  描述：

  D-葡萄糖 在 氨 作用下， 以 甲醇 为溶剂， 生成 beta-D-吡喃葡萄糖胺
  参考文献：
  名称：

  缺电子糖基胺及其衍生糖基酰胺的合成和表征

  摘要：

  本文描述了使用甲醇氨制备二糖基胺的统一方法。所有制备的糖基胺都已得到充分表征，并且它们的异头构型已被确定。该文章提出了一种二糖胺和其他缺电子糖胺的N-酰化新方法，该方法使用硝基甲烷作为溶剂在酸性条件下进行羧酸酐酰化。这种转化的可行性体现在广泛的反应底物上。所有糖基酰胺均仅由 β-构型形成。这两个反应构成了合成一类具有N-糖苷键的新型化合物的简单而有效的途径。

  DOI：

  10.1016/j.carres.2024.109023
• 作为试剂：
  描述：

  N-叔丁氧羰基-S-三苯甲基-L-半胱氨酸 在 三乙胺 、 氯甲酸异丁酯 、 beta-D-吡喃葡萄糖胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.33h， 以21%的产率得到N-(N-tert-butyloxycarbonyl-S-trityl-L-cysteinyl)-β-D-glucopyranosylamine
  参考文献：
  名称：

  GLYCOAMINO ACID AND USE THEREOF

  摘要：

  本发明的目的是提供一种氨基酸前体，该前体在氨基酸的性质（特别是水溶性、在水中的稳定性、苦味等）方面表现出改进，并且可以在体内转化为氨基酸等。本发明涉及一种氨基酸前体化合物，该化合物由以下式（I）表示： 其中每个符号如描述中所述，或其盐。

  公开号：

  US20170007709A1

文献信息

• Carbohydrate Chips for Studying High-Throughput Carbohydrate−Protein Interactions
  作者：Sungjin Park、Myung-ryul Lee、Soon-Jin Pyo、Injae Shin

  DOI：10.1021/ja0391661

  日期：2004.4.1

  diverse carbohydrate probes, solution-phase parallel and enzymatic glycosylations were performed. Three model disaccharides were in parallel synthesized in solution-phase and used as carbohydrate probes for the fabrication of carbohydrate chips. Three enzymatic glycosylations on glass slides were consecutively performed to generate carbohydrate microarrays that contained the complex oligosaccharide, sialyl

  碳水化合物-蛋白质相互作用在生物体中起着重要的生物学作用。在大多数情况下，生物物理和生物化学方法已被用于研究这些生物分子相互作用。对阐明碳水化合物和蛋白质之间识别事件的高通量方法的开发关注较少。在目前开发用于监测碳水化合物-蛋白质相互作用的新型高通量工具的努力中，我们通过将马来酰亚胺连接的碳水化合物固定在硫醇衍生的载玻片上来制备碳水化合物微阵列，并使用这些微阵列进行凝集素结合实验。结果表明，具有不同结构特征的碳水化合物以与从基于溶液的测定中获得的那些相关联的相对结合亲和力选择性地结合到相应的凝集素。此外，还通过用碳水化合物微阵列确定可溶性碳水化合物的 IC(50) 值来定量分析凝集素对碳水化合物的结合亲和力。为了制造包含更多不同碳水化合物探针的碳水化合物芯片，进行了液相平行和酶促糖基化。在溶液相中平行合成了三种模型二糖，并将其用作制备碳水化合物芯片的碳水化合物探针。连续在载玻片上进行三个酶
• Application of Squaric Acid Esters in Aminodeoxy Sugar Chemistry
  作者：Ferenc Sztaricskai、Erzsébet Roth、Mária Andrei、István F. Pelyvás、Pál Herczegh

  DOI：10.1246/cl.2007.1012

  日期：2007.8.5

  The reaction of dimethyl squarate with aminodeoxy sugars, aminodeoxy alditols, amino aldonic acids, and glycosyl amines under neutral conditions furnished the squaric amide esters, which were converted in more alkaline media (pH ≈8) into the asymmetric squaric diamides. The unprotected squaric acid amide esters are suitable for constructing a specific anchor (spacer, linker) function that favorably influences the water-solubility of the resulting drugs and glycoconjugates.

  二甲基方酸酯与氨基去氧糖、氨基去氧醇、氨基醛酸和糖基胺在中性条件下反应，生成了方酸酰胺酯，这些方酸酰胺酯在更碱性的介质（pH≈8）中转化成不对称方酸二酰胺。不受保护的方酸酰胺酯适合用于构建特定的锚固（间隔、连接）功能，这些功能对生成的药物和糖缀合物的水溶性有积极影响。
• Synthesis of Sugar Isocyanates and Their Application to the Formation of Ureido-Linked Disaccharides
  作者：Martín Ávalos、Reyes Babiano、Pedro Cintas、Michael B. Hursthouse、José L. Jiménez、Mark E. Light、Juan C. Palacios、Esther M. S. Pérez

  DOI：10.1002/ejoc.200500601

  日期：2006.2

  The present work describes a facile and practical route to carbohydrate-based isocyanates, a reactive and appealing family of chiral heterocumulenes, wich can be easily converted into disaccharides and pseudodisaccharides interconnected by urea moieties. A full characterization of these substances by X-ray diffraction analysis and spectroscopic methods reveals further insights into their structures

  目前的工作描述了一种简便实用的基于碳水化合物的异氰酸酯的途径，这是一种反应性和吸引人的手性杂草烯家族，可以很容易地转化为通过尿素部分相互连接的二糖和假二糖。通过 X 射线衍射分析和光谱方法对这些物质进行全面表征，可以进一步了解它们的结构和优选构象。
• Synthesis of Neoglycoconjugates by the Desulfurative Rearrangement of Allylic Disulfides
  作者：David Crich、Fan Yang

  DOI：10.1021/jo8015314

  日期：2008.9.19

  neoglycosyl donors are prepared on the basis of connection of an allylic disulfide motif to the anomeric center via a simple O-glycosyl linkage or N-glycosyl amide unit. Conjugation of both sets of donors to cysteine in peptides is demonstrated through classical disulfide exchange followed by the phosphine-mediated desulfurative allylic rearrangement resulting in neoglycopeptides characterized by a simple thioether

  两个系列的新糖基供体是在烯丙基二硫化物基序通过简单的 O-糖基键或 N-糖基酰胺单元连接到异头中心的基础上制备的。两组供体与肽中的半胱氨酸的缀合通过经典的二硫键交换和膦介导的脱硫烯丙基重排得到证明，从而产生以简单硫醚间隔物为特征的新糖肽。在室温下，在水性介质中，在新糖基供体和肽上均不存在保护基团的情况下，缀合反应起作用。
• The effect of monosaccharides on self-assembly of benzenetricarboxamides
  作者：Jue Wang、Wenjing Qi、Guosong Chen

  DOI：10.1016/j.cclet.2018.12.014

  日期：2019.3

  Abstract The interaction between monosaccharides exhibits an important role in the assembly of monosaccharide-containing molecules. In this work, three common monosaccharides, glucose, galactose and mannose, are employed to investigate the effect of monosaccharide on the self-assembly of benzenetricarboxamide (BTA) core-containing molecules. In the presence of monosaccharides, three benzenetricarboxamide

  摘要单糖之间的相互作用在含单糖分子的组装中起着重要作用。在这项工作中，使用三种常见的单糖，葡萄糖，半乳糖和甘露糖，来研究单糖对含苯三甲酰胺（BTA）核心分子的自组装的影响。在单糖存在下，三种苯三甲酰胺衍生物会聚集成不同的有序结构。当在核心和单糖之间的这些分子中引入丙氨酸接头时，三种类型的单糖BTA的形态变为无序，同时其结构随着丙氨酸接头长度的增加而变得相似，表明单糖作用的消失。