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2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl 2,2,2-trichloroacetimidate CAS:86520-63-0

2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl 2,2,2-trichloroacetimidate is a chemical compound commonly used in carbohydrate chemistry and glycosylation reactions. It is a derivative of α-D-galactopyranose, a type of sugar, where the hydroxyl groups on the 2, 3, 4, and 6 positions of the galactopyranose ring are acetylated. Additionally, the anomeric carbon (C1) of the sugar is protected with a trichloroacetimidate group, which makes it a strong electrophile during glycosylation reactions.

The compound is often used as a glycosylating agent to introduce galactose moieties into various molecules, such as proteins, peptides, or small organic molecules. This can be achieved by reacting this compound with a nucleophile (e.g., hydroxyl groups on the target molecule) under suitable conditions. The trichloroacetimidate group facilitates the attachment of the galactose moiety to the target molecule, resulting in the formation of a glycosidic bond.

This compound is commonly utilized in the synthesis of glycoconjugates, glycopeptides, and glycolipids. It offers a versatile and efficient method for modifying molecules with galactose residues, which can be relevant in various fields, including biological studies, drug delivery systems, or vaccine development.

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Application and Effect

Glycosylation: The compound reacts with various acceptor molecules containing hydroxyl groups, such as alcohols or amines, to form glycosidic bonds. This allows the introduction of galactose onto the acceptor molecule, resulting in the synthesis of glycoconjugates, glycopeptides, or glycolipids.

Biochemical and biological studies: The compound helps researchers study the biological functions and interactions of galactose-containing molecules. By selectively attaching galactose to proteins, peptides, or other biomolecules, researchers can investigate their roles in cellular processes, receptor-ligand interactions, and disease mechanisms.

Drug delivery systems: The compound can be used to modify drug molecules with galactose residues, facilitating targeted drug delivery to specific tissues or cells. Galactose can act as a targeting ligand, recognizing specific receptors expressed on the surface of cells, particularly hepatocytes. By attaching galactose to drugs, researchers can enhance their selectivity and efficacy in targeted therapy.

Vaccine development: Galactose-containing molecules play a crucial role in immune responses, as they are recognized by lectins present on immune cells. By conjugating antigens with galactose moieties using this compound, researchers can enhance immune responses and develop more effective vaccines.

Chemical synthesis: The compound can be employed in various chemical syntheses where galactose modifications are required. This includes the preparation of complex carbohydrate structures, oligosaccharides, or glycomimetics, which can be further utilized in medicinal chemistry or as research tools.

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Additional Information:

Composition C16H20Cl3NO10
Assay 99%
Appearance White powder
CAS No. 86520-63-0
Packing Small and bulk
Shelf Life 2 years
Storage Store in cool and dry area
Certification ISO.


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