2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 | 572-09-8

• 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: 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物
• 中文别名: 2,3,4,6-四乙酰氧基-α-D-吡喃葡萄糖溴化物；2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖酰溴；溴代葡萄糖苷；乙酰溴-Alpha-D-葡萄糖；乙酰溴-α-D-葡萄糖；溴代四乙酰基葡萄糖苷
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
• 英文别名: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triacetyl ester；(2R,3R,4S,5R,6R)-2-bromo-6-(acetyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate；tetra-O-acetyl-α-D-glucopyranosyl bromide；acetobromo-α-D-glucose；2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide；(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate；2,3,4,6-tetra-O-acetyl-α-glucopyranosyl bromide；2,3,4,6-tetraacetoxy-α-D-glucopyranose bromide；2,3,4,6-tetra-O-acetyl-α-D-glucosyl bromide；1-bromo-α-D-glucose tetraacetate；2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranose；1-bromo-2,3,4,6-tetra-O-acetyl-α-D-glucopyranose；1-bromo-2,3,4,6-tetra-O-acetyl-α-D-glucose；α-bromo-tetra-O-acetyl-glucose；α-acetobromoglucose；1-deoxy-1-bromo-2,3,4,6-tetra-O-acetyl-α-D-glucopyranose；2,3,4,6-tetra-O-acetyl-α-bromo-D-glucopyranose；tetraacetyl-α-D-glucosyl bromide；α-bromotetraacetylglucose；acetobromo-a-D-glucose；1-bromo-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；2,3,4,6-tetraacetoxy-alpha-D-glucopyranose bromide；2,3,4,6-tetra-O-acetyl-a-D-glucopyranosyl bromide；N,N-diacetylbromide-α,D-glucose；bromo-α-D-glucose tetraacetate；bromotetraacetyl glucose；ACBG；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate
• CAS: 572-09-8
• 化学式: C₁₄H₁₉BrO₉
• 分子量: 411.203
• InChiKey: CYAYKKUWALRRPA-RGDJUOJXSA-N

物化性质

• 熔点：
  86-89 °C
• 比旋光度：
  194.5 º (c=2,chloroform)
• 沸点：
  0.125-30 °C(Press: 0.0005 Torr)
• 密度：
  1.49±0.1 g/cm3(Predicted)
• 溶解度：
  乙腈（极微量）、氯仿（微量溶解）、甲醇（微量溶解）
• 稳定性/保质期：
  要避免的物料：氧化物、水分和潮湿。 要分解的产品：一氧化碳和二氧化碳、溴化氢。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• 海关编码：
  29329985
• 危险品运输编号：
  NONH for all modes of transport
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  1. 充入氩气密封、避光保存，并在-18℃的干燥环境中存放。

SDS

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Bromide Revision number: 5
(stabilized with CaCO3)
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Bromide (stabilized with CaCO3)
Product name:


Revision number: 5

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

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Bromide (stabilized with CaCO3)
Percent: >98.0%(T)
CAS Number: 572-09-8
Chemical Formula: C14H19BrO9

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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.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl
Bromide (stabilized with CaCO3)

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Section 5. FIRE-FIGHTING MEASURES
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.
When extinguishing fire, be sure to wear personal protective equipment.
Special protective
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
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
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
Storage conditions: Keep container tightly closed. Store in a freezer.
Store under inert gas.
Protect from moisture.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive, Light-sensitive, Moisture-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
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
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: White - Slightly pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:89°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
[Water] No data available
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl
Bromide (stabilized with CaCO3)

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
No data available
[Other solvents]

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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:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen bromide
products:

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

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
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
Hazards Class: Does not correspond to the classification standard of the United Nations
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.
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl
Bromide (stabilized with CaCO3)

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：这是一种极其活泼的重要中间体，可以方便地制备各种苷类衍生物。

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 喹啉 、 甲醇 、 铂 、 silver carbonate 作用下， 生成 estradiol-17β 3-β-D-glucopyranoside
  参考文献：
  名称：

  Hagedorn et al., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1940, vol. 264, p. 23,24, 25

  摘要：

  DOI：
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 乙酰溴 、 三氟化硼乙醚 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物
  参考文献：
  名称：

  对甲氧基苯基糖苷转化为相应的糖基氯化物和溴化物，并转化为硫代苯基糖苷。

  摘要：

  使用硼从相应的1-O-乙酰基糖中制备对甲氧基苯基（pMP）β-D-吡喃葡萄糖苷（Glc，Gal，GlcNPhth，GalNPhth，GlcNTroc，Gal beta 4Glc，Gal alpha 4Gal），使用硼制得三氟化醚醚为助催化剂。在各种路易斯酸的存在下用酰氯或溴化物处理pMP糖苷得到相应的糖酰氯和溴化物，产率为81-98％。用硫酚和三氟化硼醚化物处理酰基保护的pMP糖苷，可以80-100％的收率和高（> 20：1）β/ alpha选择性获得相应的硫糖苷。针对一系列试剂研究了pMP糖苷的稳定性。

  DOI：

  10.1016/s0008-6215(96)90118-4
• 作为试剂：
  描述：

  (+/-)-steganol 、 氰化汞 在 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以45%的产率得到(-)-4α-cyanostegane
  参考文献：
  名称：

  Stereoselective reactions. XVII. Absolute structure-cytotoxic activity relationships of steganacin congeners and analogs

  摘要：

  The cytotoxic activities of optically pure and racemic steganacin congeners and analogues against KB cells in culture and the inhibitor activity of cilia regeneration in Tetrahymena were studied with regard to absolute and retative configurations. The stereochemical requirements of dibenzocyclooctadiene lignan lactones for activity were clarified.

  DOI：

  10.1021/jm00105a009

文献信息

• Synthesis of phosphatidyl-β-glucosyl glycerol containing a dioleoyl diglyceride moiety
  作者：C.A.A. van Boeckel、G.M. Visser、J.H. van Boom

  DOI：10.1016/s0040-4020(01)82350-4

  日期：1985.1

  in a two step procedure, to afford compound ; (c) a 2,4-dichlorophenyl protected phosphatidic acid derivative . Compound could be selectively coupled to the primary hydroxyl function of to afford the fully protected glycophospholipid . Finally, removal of the 2,4-dichlorophenyl and TIPS protecting groups from was performed with syn-4-nitrobenzaldoximate and fluoride ions, respectively, to afford glycophospholipid

  描述了磷脂酰-β-葡萄糖基甘油二酸酯的制备。糖脂的合成是通过以下方法完成的：（a）暂时保留左旋糖基的葡糖羟基功能，然后可以将其转化为被二油酰基取代的衍生物；（b）在两步法中，四异丙基二硅氧烷-1，3-二基（TIPS）基团保护其的3'-和4'-羟基，得到化合物；（c）2，4-二氯苯基保护的磷脂酸衍生物。化合物可以选择性地与的伯羟基功能偶合，以提供充分保护的糖磷脂。最后，去除2,4-二氯苯基和TIPS保护基分别用4-硝基苯并氧肟酸和氟离子进行操作，得到糖脂。
• Streptococcus pneumoniae type XIV polysaccharide: synthesis of a repeating branched tetrasaccharide with dioxa-type spacer-arms
  作者：Paul-Henri Amvam-Zollo、Pierre Sinaÿ

  DOI：10.1016/0008-6215(86)80016-7

  日期：1986.8

  beta-Glycosides of 2-acetamido-2-deoxy-D-glucopyranose were synthesised, using either 7-methoxycarbonyl-3,6-dioxa-1-heptanol or 8-azido-3,6-dioxa-1-octanol. Selective beta-lactosylation of 7-methoxycarbonyl-3,6-dioxaheptyl 2-acetamido-3-O-benzyl-2-deoxy-beta-D-glucopyranoside with hepta-O-acetyl-lactosyl-trichloroacetimidate, followed by beta-galactosylation of the secondary hydroxyl group with O-(2

  使用7-甲氧基羰基-3,6-二氧杂-1-庚醇或8-叠氮基3,6-二氧杂-1-辛醇合成了2-乙酰氨基-2-脱氧-D-吡喃葡萄糖的β-糖苷。7-甲氧基羰基-3,6-二氧杂庚基2-乙酰氨基-3-O-苄基-2-脱氧-β-D-吡喃葡萄糖苷与七-O-乙酰基-乳糖基-三氯乙酰胺酸的选择性β-乳糖基化，然后β-半乳糖基化仲羟基与O-（2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基）三氯乙酰亚胺基，催化氢解和O-脱乙酰化，得到7-甲氧基羰基-3,6-二氧杂庚基2 -乙酰氨基-2-脱氧-4-O-β-D-吡喃半乳糖基-6-O-（4-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖基）-β-D-吡喃葡萄糖苷。8-azido-3的选择性β-乳糖基化
• A Novel Approach for the Formation of Carbon−Nitrogen Bonds:  Azidation of Alkyl Radicals with Sulfonyl Azides
  作者：Cyril Ollivier、Philippe Renaud

  DOI：10.1021/ja004129k

  日期：2001.5.1

  Two preparatively attractive methods for the azidation of alkyl radicals are described. Secondary and tertiary alkyl iodides and dithiocarbonates are easily converted into the corresponding azides, either by reaction with ethanesulfonyl azide in the presence of dilauroyl peroxide, or by treatment with benzenesulfonyl azide and hexabutylditin in the presence of a radical initiator. Interestingly, intramolecular

  描述了用于烷基基团叠氮化的两种制备性有吸引力的方法。通过在过氧化二月桂酰存在下与乙磺酰叠氮化物反应，或在自由基引发剂存在下用苯磺酰叠氮化物和六丁基二锡处理，仲和叔烷基碘和二硫代碳酸酯很容易转化为相应的叠氮化物。有趣的是，分子内串联自由基环化-叠氮化过程可以以高产率进行。
• [EN] CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE RÉTICULATION ET PROCÉDÉS D'UTILISATION
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2021016537A1

  公开（公告）日：2021-01-28

  Compounds comprising a cross-linking moiety and a protecting group are described herein along with their methods of use. The cross-linking moiety may comprise an indoxyl and the protecting group may comprise a sugar (e.g., a glucuronide or glucoside), phosphoester, or sulfoester group. The cross-linking moiety and protecting group may be attached to each other via an oxygen atom, sulfur atom, or linker. In some embodiments, the linker attaching the cross-linking moiety and protecting group is a self-immolative linker. A compound of the present invention may cross-link under physiological conditions and/or in vivo.

  本文描述了包含交联基团和保护基团的化合物，以及它们的使用方法。交联基团可能包括吲哚基团，保护基团可能包括糖类（例如葡萄糖醛酸盐或葡萄糖苷）、磷酸酯或磺酸酯基团。交联基团和保护基团可以通过氧原子、硫原子或连接剂相互连接。在某些实施例中，连接交联基团和保护基团的连接剂是自解离连接剂。本发明的化合物可能在生理条件和/或体内发生交联。
• Design, Synthesis and In Vivo Evaluation of Sulfhydryl &amp;#946;-D-Glucose Cholesterols as Ligands for Brain Targeting Liposomes
  作者：Wei Fan、Chengyi Yan、Shan Qian、Nian Yao、Lei Tang、Yong Wu

  DOI：10.2174/157018010790945788

  日期：2010.5.1

  A novel sulfhydryl-β-D-glucose cholesterol 10a-10f as ligand for brain targeting liposomes was designed and synthesized. 10e was applied to the preparation of liposomal delivery system for achieving the brain-targeted delivery of the model drug tegafur in mice utilizing the glucose transporter member 1 (GLUT1). The results suggest the feasibility to enhance liposomes ability of delivering drug to brain by using the designed compound as liposome ligands.

  设计并合成了一种新型硫醇-β-D-葡萄糖胆固醇10a-10f作为脑靶向脂质体的配体。应用10e制备脂质体递送系统，旨在利用葡萄糖转运蛋白成员1（GLUT1）在 mice 中实现模型药物替加氟的脑靶向递送。结果表明，通过使用设计的化合物作为脂质体配体，可以增强脂质体向脑内递送药物的能力。