2,3,4,6-Tetra-O-benzyl-D-galactopyranose Trichloroacetimidate

2,3,4,6-Tetra-O-benzyl-D-galactopyranose Trichloroacetimidate

2,3,4,6-Tetra-O-benzyl-D-galactopyranose trichloroacetimidate is a carbohydrate derivative used extensively in organic synthesis, particularly in glycosylation reactions. This compound is characterized by its protective benzyl groups and a reactive trichloroacetimidate functionality, making it a valuable tool for the synthesis of complex carbohydrates and glycoconjugates.

Chemical Identity

• CAS Number: 132748-02-8
• MDL Number: MFCD07369660
• Catalog Number: A1251105
• Molecular Formula: C₃₆H₃₆Cl₃NO₆
• Molecular Weight: 685.03 g/mol
• IUPAC Name: 2,2,2-Trichloro-N-[(3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetamide

Physical Properties

• Appearance: Yellow viscous liquid
• Melting Point: 78–79 °C
• Boiling Point: Not explicitly listed but stable under standard laboratory conditions.
• Density: Not specified; expected to be typical for viscous organic liquids.
• Storage Conditions: Store at 2–8°C for long-term stability (months).

Structural Features

This compound features:

• A D-galactopyranose backbone with four benzyl groups attached at the 2, 3, 4, and 6 positions.
• A trichloroacetimidate group at the anomeric position (C1), which enhances its reactivity in glycosylation processes.
• The benzyl groups serve as protective groups that prevent unwanted reactions at hydroxyl sites during synthesis.

Applications

2,3,4,6-Tetra-O-benzyl-D-galactopyranose trichloroacetimidate is utilized in various fields:

1. Organic Synthesis:
   • Acts as a glycosyl donor for synthesizing oligosaccharides and glycoconjugates.
   • Used in the preparation of glycosides and other carbohydrate derivatives.
2. Pharmaceutical Research:
   • Plays a role in developing carbohydrate-based drugs and enzyme inhibitors.
   • Facilitates the synthesis of bioactive molecules for therapeutic applications.
3. Biochemical Studies:
   • Employed in research involving carbohydrate-protein interactions.
   • Useful for studying enzymatic mechanisms related to glycosidic bond formation.

Safety and Handling

• Hazard Statements: Generally considered safe when handled properly; however, standard laboratory precautions should be observed due to the presence of reactive trichloroacetimidate groups.
• Storage Conditions: Store in a cool, dry place away from moisture in tightly sealed containers.

Regulatory Information

This compound complies with TSCA regulations but should be verified for specific handling requirements based on local laws and regulations.

2,3,4,6-Tetra-O-benzyl-D-galactopyranose trichloroacetimidate is commercially available for research purposes and is integral to advancing carbohydrate chemistry. Its unique structure allows for versatile applications in synthetic and analytical chemistry.

Citations:

1. http://chemsynlab.com/en/product/132748-02-8.html
2. https://www.sigmaaldrich.com/IN/en/product/sial/03701
3. https://pubchem.ncbi.nlm.nih.gov/compound/16211056
4. https://www.chemicalbook.in/cas/132748-02-8.htm
5. https://www.chemicalregister.com/2_3_4_6-Tetra-O-benzyl-D-galactopyranose_Trichloroacetimidate/Suppliers/pid585754.htm
6. https://www.chemsrc.com/en/cas/167904-03-2_230827.html
7. https://chembk.com/en/p/342347
8. https://en.wikipedia.org/wiki/Tetrasodium_EDTA