2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride is a chemically synthesized amino sugar derivative, featuring a glucopyranosyl ring where the hydroxyl groups at positions 3, 4, and 6 are protected by acetyl groups, the 2-position is substituted with an acetamido group, and the anomeric carbon forms a glycosyl chloride in the α-configuration. This compound is a white crystalline solid widely employed as a reactive intermediate in glycosylation chemistry particularly in the synthesis of N-acetylglucosamine derivatives and glycoconjugates. The acetamido group at C2 is critical for biologically relevant carbohydrate structures such as glycoproteins and bacterial cell wall components. The molecular formula is C13H18ClNO8 with a molecular weight around 365.73 g/mol. It is prepared through selective acetylation and halogenation of glucosamine derivatives, purified to high purity (>95%), and quality-controlled by NMR, MS, and HPLC. The compound typically exhibits minimal microbial contamination due to its synthetic origin. Proper storage in a refrigerated, moisture-sealed container extends its shelf life to 1–2 years. It is applied extensively in medicinal chemistry, glycobiology research, and synthetic organic chemistry to develop bioactive conjugates and molecular probes.IUPAC Name

• 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride

Appearance

• White crystalline powder

Source

• Synthesized via selective acetylation of glucosamine followed by halogenation at the anomeric carbon
• Rigorous purification under controlled laboratory conditions

Molecular Weight and Structure

• Molecular Formula: C13H18ClNO8
• Molecular Weight: 365.73 g/mol
• Structure: α-D-glucopyranosyl ring, acetamido substituent at C2, acetyl groups at C3, C4 and C6, and chlorine at anomeric C1

Sugar Specificity

• N-acetylglucosamine (GlcNAc) derivative with α configuration at the anomeric center
• Reflects structures found in glycoproteins and bacterial cell walls

Biological Activity

• Serves as an intermediate for synthesizing biologically relevant N-acetylglucosamine conjugates
• Enables studies on glycosyltransferase specificity and carbohydrate-protein interactions
• May serve as a prodrug linker or molecular probe precursor

Purity and Microbial Contamination

• Purity typically above 95%, confirmed by NMR and chromatography
• Synthetic process ensures minimal microbial contamination

Identity and Quality Control

• Confirmed by 1H, 13C NMR, mass spectrometry, and HPLC chromatograms
• Certificates of Analysis and Safety Data Sheets provided

Shelf Life and Storage

• Store in dry, sealed containers at 2–8 °C
• Protect from moisture and light
• Stable for 1–2 years under recommended storage

Application

• Intermediate in chemical synthesis of glycoproteins, glycoconjugates, and glycomimetics
• Used in enzymatic and structural studies of N-acetylglucosamine-containing biomolecules
• Supports medicinal chemistry and drug development involving carbohydrate linkers and analogs

Key Characteristics

• Acetylated and acetamido-substituted α-GlcNAc glycosyl chloride
• CAS Number: 98545-12-1
• Molecular Weight: 365.73 g/mol
• White crystalline solid, high purity
• Useful for regio- and stereoselective glycosylation
• Provided with rigorous analytic characterization
• Stable under refrigeration with moisture protection

Citations

• AnaxLab detailed profile​
• CalpacLab synthesis and properties​
• PubChem molecular data​
• Sigma-Aldrich glycoside reagents​
• MedChemExpress carbohydrate probes
• PMC enzymology and glycobiology articles​
• Synthose chemical catalog
• Patent literature on glycosyl chlorides
• Benchchem product specifications​
• ScienceDirect glycan synthesis reviews​