3,4,6-Tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

3,4,6-Tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

3,4,6-Tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose is a chemically modified carbohydrate that serves as an important intermediate in carbohydrate chemistry. This compound is characterized by its protective acetyl groups and a methoxyethylidene group, which enhance its reactivity and stability for further synthetic applications.

Chemical Identity

• CAS Number: 4435-05-6
• Product Code: A1247723
• IUPAC Name: 1,2-O-(1-methoxyethylidene)-3,4,6-tri-O-acetyl-β-D-mannopyranose
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.33 g/mol

Physical Properties

• Appearance: Colorless to pale yellow syrup or viscous liquid
• Purity: ≥95% (commonly verified via NMR spectroscopy)
• Boiling Point: Not explicitly listed but typically stable under standard laboratory conditions.
• Solubility: Soluble in polar organic solvents such as methanol, dimethyl sulfoxide (DMSO), and dichloromethane; insoluble in water.

Structural Features

This compound features:

• A β-D-mannopyranose backbone with three acetyl groups at the 3, 4, and 6 positions.
• An acetal linkage with a methoxyethylidene group at the anomeric position (C1), which enhances the compound’s stability and reactivity.
• The acetyl groups serve to protect the hydroxyl functionalities during chemical reactions.

Applications

3,4,6-Tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose is utilized in various fields:

• Organic Synthesis: Acts as a glycosyl donor in glycosylation reactions for synthesizing complex carbohydrates and glycoconjugates.
• Pharmaceutical Research: Used in the development of carbohydrate-based drugs and enzyme inhibitors due to its ability to modulate biological activity.
• Biochemical Studies: Employed in research involving carbohydrate-protein interactions and enzymatic mechanisms.

Safety and Handling

• Hazard Statements: Generally considered safe when handled properly; however, standard laboratory precautions should be observed.
• Storage Conditions: Store at -20°C in a tightly sealed container to prevent moisture absorption.

Regulatory Information

This compound is expected to comply with TSCA regulations but should be verified for specific handling requirements based on local regulations.

3,4,6-Tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose is commercially available for research purposes and is integral to advancing carbohydrate chemistry and related fields.

Citations:

1. https://www.rsc.org/suppdata/d0/ra/d0ra01128b/d0ra01128b1.pdf
2. https://synthose.com/products/TL529
3. https://pmc.ncbi.nlm.nih.gov/articles/PMC7429366/
4. https://synthose.com/products/TM584
5. https://ie.vwr.com/store/product/34584542/3-4-6-tri-o-acetyl-1-2-o-1-methoxyethylidene-d-mannopyranose-98
6. https://ie.vwr.com/store/category/3-4-6-tri-o-acetyl-1-2-o-1-methoxyethylidene-d-mannopyranose/34552839
7. https://www.sigmaaldrich.com/US/en/product/aldrich/r533483
8. https://academic.oup.com/bcsj/article-pdf/59/5/1581/55720293/bcsj.59.1581.pdf