2,3,4,6-四-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 | 86520-63-0

• 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-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯
• 中文别名: 2,3,4,6-四-O-乙酰基-Α-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate
• 英文别名: 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl trichloroacetimidate；O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl) trichloroacetimidate；2,3,4,6-tetra-O-acetyl-α-D-galactosyl trichloroacetimidate；2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl trichloroacetamidate；2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside；2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 86520-63-0
• 化学式: C₁₆H₂₀Cl₃NO₁₀
• 分子量: 492.695
• InChiKey: IBUZGVQIKARDAF-MBJXGIAVSA-N

物化性质

• 熔点：
  121 °C
• 沸点：
  463.3±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 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：
  148
• 氢给体数：
  1
• 氢受体数：
  11

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  Freezer

SDS

2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl 2,2,2- Revision number: 5
Trichloroacetimidate
SAFETY DATA SHEET

---

Section 1. IDENTIFICATION
2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl 2,2,2-Trichloroacetimidate
Product name:


Revision number: 5

---

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

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl 2,2,2-Trichloroacetimidate
Percent: >93.0%(LC)
CAS Number: 86520-63-0
Chemical Formula: C16H20Cl3NO10

---

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.

---

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-galactopyranosyl
2,2,2-Trichloroacetimidate

---

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:

---

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.

---

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 away from incompatible materials such as oxidizing agents.
Heat-sensitive
Packaging material: Comply with laws.

---

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.

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: Very pale yellow - Pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:122°C
Boiling point/range: No data available
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
[Other solvents] No data available
2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl
2,2,2-Trichloroacetimidate

---

Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen chloride
products:

---

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

---

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):

---

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.

---

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

---

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-galactopyranosyl
2,2,2-Trichloroacetimidate

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷
  参考文献：
  名称：

  [EN] METHOD OF PREPARATION OF 6-AZIDO-2,4-DIACETAMIDO-2,4,6-TRIDEOXY-D-MANNOSE
  [FR] PROCÉDÉ DE PRÉPARATION DE 6-AZIDO-2,4-DIACÉTAMIDO-2,4,6-TRIDÉOXY-D-MANNOSE

  摘要：

  该发明涉及一种制备6-叠氮基-2,4-二乙酰氨基-2,4,6-三去氧-D-甘露糖的方法。该方法包括化合物(X)的化学反应。其中：R1可以是C1到C6的烷基，包括甲基、乙基、异丙基；芳基，包括苯基；这些基团可以被取代或未取代；R2可以是C1到C6的烷基，包括甲基、乙基、异丙基、叔丁基、异丁基；这些基团可以被取代或未取代；与包含Lewis酸或Bronsted酸的脱保护试剂在极性无水溶剂中发生化学反应，从而获得一个自由的C-1 OH基团。该方法也可以从商业上可获得的D-半乳糖五乙酰基、D-半乳糖四乙酰基或四乙酰基D-半乳糖基三氯乙酰亚胺开始制备。根据该发明，去保护异构位置的步骤避免了使用铈，并且可以方便地纯化6-叠氮基-2,4-二乙酰氨基-2,4,6-三去氧-D-甘露糖。

  公开号：

  WO2017085145A1
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 2,3,4,6-四-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯
  参考文献：
  名称：

  具有芳香族基团和各种脂肪酰基侧链的基​​于苏氨酸的半乳糖酰胺的设计，合成和细胞毒性评估

  摘要：

  摘要在半乳糖神经酰胺中，酰胺部分或植物鞘氨醇基团上存在脂肪酰基是影响细胞毒性的一些重要特征。正在进行不断的努力来修饰半乳糖神经酰胺上存在的脂肪酸部分和植物鞘氨醇基团，以增强这些化合物的细胞毒性潜力。因此，在本研究中，通过使用三氯乙亚氨酸酯方法用不同的脂肪酰基部分和芳族酸修饰酰胺部分上的脂肪酰基，从而制得基于苏氨酸的β-半乳糖神经酰胺及其衍生物。与结构相关的基于苏氨酸的神经酰胺部分是使用不同的试剂通过多步过程合成的。使用三氯乙酰亚胺酸酯作为供体，用半乳糖将神经酰胺部分糖基化。进一步，评价所有合成的化合物对三种癌细胞系和一种正常细胞系的体外细胞毒性，并且所有化合物对所有测试的癌细胞系均表现出良好至中等的细胞毒性。在芳族衍生物中，该化合物8i对MCF7，A549和HeLa癌细胞系表现出有希望的活性，其IC 50值分别为14.08、14.78和16.70 µM。在脂肪酸衍生物中，两种化合物表现出良

  DOI：

  10.1007/s00044-017-2049-9

文献信息

• 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
• [EN] COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF<br/>[FR] COMPOSÉS COMPRENANT UN LIEUR CLIVABLE ET LEURS UTILISATIONS
  申请人：INTOCELL INC

  公开号：WO2019008441A1

  公开（公告）日：2019-01-10

  Provided are a compound including a cleavable linker, a use thereof, and an intermediate compound for preparing the same, and more particularly, the compound including a cleavable linker of the present invention may include an active agent (for example, a drug, a toxin, a ligand, a probe for detection, etc.) having a specific function or activity, a SO2 functional group which is capable of selectively releasing the active agent, and a functional group which triggers a chemical reaction, a physicochemical reaction and/or a biological reaction by external stimulation, and may further include a ligand (for example, oligopeptide, polypeptide, antibody, etc.) having binding specificity for a desired target receptor.

  提供了一种包括可切割连接物的化合物，其用途，以及用于制备该化合物的中间体化合物，更具体地，本发明的包括可切割连接物的化合物可能包括具有特定功能或活性的活性剂（例如，药物，毒素，配体，用于检测的探针等），能够选择性释放活性剂的SO2官能团，以及通过外部刺激触发化学反应，物理化学反应和/或生物反应的官能团，并且还可以包括具有与所需靶受体结合特异性的配体（例如，寡肽，多肽，抗体等）。
• 三糖对甲氧基苯酚苷类化合物及其制备方法
  申请人：中国人民解放军第二军医大学

  公开号：CN106565800B

  公开（公告）日：2019-08-13

  本发明涉及一种基于炭疽荚膜表面糖抗原的新型三糖对甲氧基苯酚苷类化合物及其制备方法。所述的三糖对甲氧基苯酚苷类化合物的结构式为：其中的R1是乙酰基，R2是苄基，R3是乙酰氨基，端位是对甲基苯氧基。本发明的化合物可用于制备类寡糖缀合物，并用于炭疽糖疫苗的合成研究，本发明化合物的合成路线简洁，操作简单，原料成本低，通用性强，糖基化反应立体选择性好，适用于各类寡糖化合物的合成。
• BIFUNCTIONAL CYTOTOXIC AGENTS CONTAINING THE CTI PHARMACOPHORE
  申请人：Pfizer Inc.

  公开号：US20160271270A1

  公开（公告）日：2016-09-22

  The present invention is directed to novel bifunctional CTI-CTI and CBI-CTI dimers of the formula: F 1 -L 1 -T-L 2 -F 2 where F 1 , L 1 , T, L 2 and F 2 are as defined herein, useful for the treatment for proliferative diseases, where the inventive dimers can function as stand-alone drugs, payloads in antibody-drug-conjugates (ADCs), and linker-payload compounds useful in connection with the production or administration of such ADCs; and to compositions including the aforementioned dimers, linker-payloads and ADCs, and methods for using these dimers, linker-payloads and ADCs, to treat pathological conditions including cancer.

  本发明涉及新颖的具有双重功能的CTI-CTI和CBI-CTI二聚物，其公式为： F1-L1-T-L2-F2 其中F1、L1、T、L2和F2如本文所述定义，用于治疗增殖性疾病，其中发明的二聚物可以作为独立药物、抗体药物偶联物（ADCs）中的有效载荷以及与生产或施用此类ADCs相关的连接器有效载荷化合物；以及包括前述二聚物、连接器有效载荷和ADCs的组合物，以及使用这些二聚物、连接器有效载荷和ADCs治疗包括癌症在内的病理状况的方法。
• Synthesis of an Isotopically-labelled Antarctic Fish Antifreeze Glycoprotein Probe
  作者：Joanna M. Wojnar、Clive W. Evans、Arthur L. DeVries、Margaret A. Brimble

  DOI：10.1071/ch10464

  日期：——

  Antifreeze glycoproteins (AFGPs) are glycosylated polypeptides produced by Antarctic and Arctic fishes, which allow them to survive in seawater at sub-zero temperatures. An investigation into the postulated enteric uptake of AFGP synthesized in the exocrine pancreas of Antarctic fishes required a custom-prepared AFGP probe that incorporated seven isotopically-labelled Ala residues for detection by

  抗冻糖蛋白（AFGP）是南极和北极鱼类产生的糖基化多肽，可以使它们在低于零温度的海水中生存。对南极鱼类外分泌胰腺中合成的AFGP的假定肠摄取的调查，需要定制的AFGP探针，该探针结合了7个同位素标记的Ala残基，用于质谱检测。的AFGPs由重复的三个氨基酸单元（丙氨酸-丙氨酸-苏氨酸），其中，所述苏氨酸残基是糖基化与二糖的β- d -Gal-（1→3）-α- d -GalNAc。同位素标记的AFGP8（1）的合成，以及受保护的糖基化氨基酸构件2的优化合成，已报告。