Α-D-五乙酸甘露糖酯 | 25941-03-1

• 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
• 中文名称: Α-D-五乙酸甘露糖酯
• 中文别名: D-吡喃甘露糖 1,2,3,4,6-五乙酸酯；1,2,3,4,6-五-O-乙酰基-D-吡喃甘露糖；α-D-五乙酸甘露糖酯；D-吡喃甘露糖1,2,3,4,6-五乙酸酯
• 英文名称: D-Mannose pentaacetate
• 英文别名: 1,2,3,4,6-penta-O-acetyl-D-mannopyranoside；mannose penta-acetate；penta-O-acetyl D-mannopyranose；1,2,3,4,6-Penta-O-acetyl-D-mannopyranose；[(2R,3R,4S,5S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate
• CAS: 25941-03-1
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: LPTITAGPBXDDGR-WHWZVRATSA-N

物化性质

• 熔点：
  68-70°C
• 沸点：
  434.8±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  溶于可溶于二氯甲烷、乙醚、乙酸乙酯、甲醇和氯仿。

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

安全信息

• 安全说明：
  S24/25
• 海关编码：
  29400090
• 危险性防范说明：
  P264,P270,P301+P312,P330
• 危险性描述：
  H302
• 储存条件：
  -20°C冷冻库

SDS

1,2,3,4,6-Penta-O-acetyl-D-mannopyranose Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1,2,3,4,6-Penta-O-acetyl-D-mannopyranose

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1,2,3,4,6-Penta-O-acetyl-D-mannopyranose
Percent: >97.0%(GC)
CAS Number: 25941-03-1
Chemical Formula: C16H22O11

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
1,2,3,4,6-Penta-O-acetyl-D-mannopyranose

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Section 5. FIRE-FIGHTING MEASURES
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Keep container tightly closed. Store in a refrigerator.
Storage conditions:
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Solid
Physical state (20°C):
Form: Crystal- Powder
Colour: White - Almost white
Odour: No data available
pH: No data available
Melting point/freezing point:68°C
Boiling point/range: No data available
No data available
Flash point:
Flammability or explosive
limits:
Lower: No data available
No data available
Upper:
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
1,2,3,4,6-Penta-O-acetyl-D-mannopyranose

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Section 10. STABILITY AND REACTIVITY
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
No data available
Log Pow:
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Does not correspond to the classification standard of the United Nations
Hazards Class:
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
1,2,3,4,6-Penta-O-acetyl-D-mannopyranose

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SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2,3,4,6-O-四乙酰基-D-吡喃甘露糖	2,3,4,6-tetra-O-acetyl-D-mannopyranose	140147-37-1	C14H20O10	348.307
  ——	tetra-acetyl glucosamine	26108-75-8	C14H21NO9	347.322
  ——	mannosan	14168-65-1	C6H10O5	162.142
  D-甘露糖	alpha-D-mannopyranoside	7296-15-3	C6H12O6	180.158
  甘露糖	D-Mannose	530-26-7	C6H12O6	180.158
  D-葡萄糖	D-glu	2280-44-6	C6H12O6	180.158
  ——	D-mannose	552-76-1	C6H12O6	180.158
  ——	2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine	——	C14H21NO9	347.322

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	β-D-mannopyranose pentaacetate	——	C16H22O11	390.344
  1,3,4,6-四-氧-乙酰-Β-D-吡啶甘露糖	1,3,4,6-tetra-O-acetyl-β-D-mannopyranose	18968-05-3	C14H20O10	348.307
  甲基四-O-乙酰基-alpha-D-吡喃甘露糖苷	methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	5019-24-9	C15H22O10	362.334
  ——	Allyl 2,3,4,6-Tetra-O-acetyl-β-D-mannopyranoside	119111-32-9	C17H24O10	388.372
  ——	1-O-(2,3,4,6-tetraacetyl-D-mannoside)-2-bromoethane	——	C16H23BrO10	455.257
  2,3,4,6-四-O-乙酰基-BETA-D-吡喃甘露糖	2,3,4,6-tetra-O-acetyl-D-mannopyranose	57884-82-9	C14H20O10	348.307
  2,3,4,6-四-O-乙酰基吡喃己糖	2,3,4,6-tetra-O-acetyl-α-D-mannopyranose	22860-22-6	C14H20O10	348.307
  2,3,4,6-O-四乙酰基-D-吡喃甘露糖	2,3,4,6-tetra-O-acetyl-D-mannopyranose	140147-37-1	C14H20O10	348.307
  ——	(1S,2R,5S)-(+)-menthyl 2,3,4,6-tetrakis-O-acetyl-α-D-mannopyranoside	——	C24H38O10	486.56
  ——	3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose	4435-05-6	C15H22O10	362.334

反应信息

• 作为反应物：
  描述：

  Α-D-五乙酸甘露糖酯 在 甲醇 、 dichlorotetrakis(1,1- dimethylethyl)di-μ-hydroxyditin 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 phenyl 2,3,4-tri-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  作为特异性诊断试剂的氟化酮庚糖的合成

  摘要：

  报道了使用亲电或亲核氟化的六种区域异构体单和二氟化 D-甘露庚酮糖和 Kamusol 类似物的直接合成。D-甘露-庚酮糖在体内显示出有吸引力的药理学特性，例如抗肿瘤活性，以及​​与胰腺β细胞结合并在其中积累以诱导高血糖。合成的类似物代表了通过 19F MRI 技术检测和量化体内 β 细胞的有希望的探针，这有助于研究疾病进展。此外，它们是抑制肿瘤生长的潜在候选物。

  DOI：

  10.1002/ejoc.201101238
• 作为产物：
  描述：

  D-葡萄糖 生成 Α-D-五乙酸甘露糖酯
  参考文献：
  名称：

  ICHIKAWA, SHUJI;TOMITA, ISAO;HOSAKA, AKIRA;SATO, TADASHI, BULL. CHEM. SOC. JAP., 61,(1988) N 2, 513-520

  摘要：

  DOI：

文献信息

• A Concise Synthesis of Oligosaccharides Derived From Lipoarabinomannan (LAM) with Glycosyl Donors Having a Nonparticipating Group at C2
  作者：Zhihao Li、Changping Zheng、Marco Terreni、Teodora Bavaro、Matthieu Sollogoub、Yongmin Zhang

  DOI：10.1002/ejoc.201901915

  日期：2020.4.16

  is one of the top ten leading causes of death over the world, and lipoarabinomannan (LAM) has been confirmed to play significant roles in this process. In this study, a convenient synthetic approach has been developed for the synthesis of oligosaccharides derived from LAM starting with commercially available substrates and reagents. The key steps for stereoselective construction of glycosidic bonds by

  导致结核病 (TB) 的分枝杆菌感染是全球十大主要死亡原因之一，而脂阿拉伯甘露聚糖 (LAM) 已被证实在此过程中发挥着重要作用。在这项研究中，开发了一种方便的合成方法，用于从市售底物和试剂开始合成源自 LAM 的寡糖。实现了在没有相邻参与组的情况下通过与供体糖基化的受体立体选择性构建糖苷键的关键步骤。值得注意的是，采用酶水解制备甘露糖结构单元，并采用桦木反应一步法脱去乙酰基和苄基以及还原叠氮基，避免了多次化学过程。最后，
• 磷酰甘露五糖及其衍生物，及其制备方法和应 用
  申请人：如东瑞恩医药科技有限公司

  公开号：CN106608893B

  公开（公告）日：2021-06-01

  本发明提出了如式(I)所示的磷酰甘露五糖及如式(II)‑(XI)所示的磷酰甘露五糖的衍生物，以及其制备方法。本发明制备方法中，通过设计甘露糖硫苷给体中羟基的保护基来调控反应活性，且在糖基化反应中副反应少，反应收率高，适宜大规模及模块化组合合成。本发明中的磷酰甘露五糖及其衍生物具有抑制血管生成的活性，具有作为抗肿瘤药物的应用前景。
• Efficient assembly of oligomannosides using the hydrophobically assisted switching phase method
  作者：Shuai Meng、Tian Tian、Dong Han、Lin-Na Wang、Shao-Geng Tang、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1039/c5ob00730e

  日期：——

  The hydrophobically assisted switching phase (HASP) method was applied in the assembly of oligomannosides.

  水疏水辅助开关相（HASP）方法被应用于寡甘露糖的组装。
• Large‐scale Synthesis of Per‐<i>O</i>‐acetylated Saccharides and Their Sequential Transformation to Glycosyl Bromides and Thioglycosides
  作者：Li‐Cheng Huang、Pi‐Hui Liang、Ching‐Yang Liu、Chun‐Cheng Lin

  DOI：10.1080/07328300600770469

  日期：2006.6

  This work describes a large‐scale synthesis of per‐O‐acetylated mono‐ and disaccharides using a stoichiometric amount of acetic anhydride in the presence of LiClO4 under solvent‐free conditions. The peracetylated saccharides underwent subsequent anomeric bromination and thioglycosidation in one‐pot to yield synthetically valuable building blocks.

  这项工作描述了在无溶剂条件下，在LiClO4存在下，使用化学计量的乙酸酐大规模合成过O-乙酰化的单糖和二糖。过乙酰化的糖随后在一个锅中进行异头溴化和硫糖苷化反应，以产生具有合成价值的结构单元。
• Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin
  作者：Melanie Rauschenberg、Eva-Corrina Fritz、Christian Schulz、Tobias Kaufmann、Bart Jan Ravoo

  DOI：10.3762/bjoc.10.138

  日期：——

  two carbohydrates. The selectivity of the synthetic lectin was investigated by incubation on the immobilized carbohydrates. Selective binding of the synthetic lectin to immobilized NANA and beta-D-galactose was observed by fluorescence microscopy. The selectivity and affinity of the synthetic lectin was screened in competition experiments. In addition, the carbohydrate binding of the synthetic lectin

  碳水化合物和蛋白质的分子识别介导了广泛的生理过程，合成碳水化合物受体（“合成凝集素”）的发展构成了生物医学技术的关键进步。在这篇文章中，我们报告了一种合成凝集素，它选择性地与固定在分子单层中的碳水化合物结合。受我们之前工作的启发，我们制备了一种荧光标记的合成凝集素，由三肽 Cys-His-Cys 的环状二聚体组成，其通过单体的空气氧化自发形成。N-乙酰神经氨酸 (NANA)、β-D-半乳糖、β-D-葡萄糖和 α-D-甘露糖的胺系衍生物微接触印在环氧化物终止的自组装单层上。连续打印产生了两种碳水化合物的简单微阵列。通过在固定化碳水化合物上孵育来研究合成凝集素的选择性。通过荧光显微镜观察合成凝集素与固定化 NANA 和β-D-半乳糖的选择性结合。在竞争实验中筛选了合成凝集素的选择性和亲和力。此外，将合成凝集素的碳水化合物结合与凝集素伴刀豆球蛋白 A 和花生凝集素的碳水化合物结合进行了比较。发现