1,2,4,6-Tetra-O-acetyl-3-deoxy-D-glucopyranose

1,2,4,6-Tetra-O-acetyl-3-deoxy-D-glucopyranose is a synthetic sugar derivative widely used in carbohydrate chemistry for constructing oligosaccharides and glycoconjugates with modified sugar residues. Derived from D-glucose, it selectively lacks the hydroxyl group at the 3-position (hence “3-deoxy”) while the hydroxyls at positions 1, 2, 4, and 6 are protected by acetyl groups. This acetylation protects those sites and allows for controlled glycosylation reactions during synthesis, enabling the creation of complex carbohydrates with defined linkages and structures. The absence of the 3-hydroxyl introduces unique conformational changes and impacts biological recognition when incorporated into oligosaccharides, making it valuable for studying enzyme binding and receptor interactions.

IUPAC Name

• (2R,4R,5S,6R)-2-(Acetoxymethyl)-6-(acetyloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Appearance

• Typically a white to off-white crystalline solid or powder.

Source

• This compound is synthetically derived from D-glucose or related sugars via a multi-step chemical process involving selective deoxygenation at C3 and acetylation at C1, C2, C4, and C6. It is not naturally occurring.

Molecular Weight and Structure

• Molecular Formula: C14H20O9
• Molecular Weight: 332.30 g/mol
• Structure: Features a 6-membered pyranose ring lacking hydroxyl at C3. Acetyl groups (–COCH3) protect hydroxyls at C1, C2, C4, and C6. The compound exists as either α or β anomer at the anomeric carbon.

Sugar Specificity

• As a chemically modified sugar building block, it lacks inherent sugar-binding specificity but serves to generate novel oligosaccharides and glycoconjugates with altered biological recognition.

Biological Activity

• The compound itself shows no significant biological activity; its value is in enabling synthesis of glycosides or oligosaccharides that can alter binding affinity and selectivity towards enzymes, receptors, or antibodies. The 3-deoxy modification can affect conformation and thus biological interactions.

Purity and Microbial Contamination

• High purity (>98%) is essential for synthesis and biological studies, determined by methods like HPLC, TLC, GC, and NMR. Microbial contamination is generally not a concern unless intended for biological assays, in which sterility testing may apply.

Identity and Quality Control

• Confirmed by ^1H and ^13C NMR spectroscopy, mass spectrometry, melting point analysis, purity assays, and water content determination (Karl Fischer titration).

Shelf Life and Storage

• Shelf life spans several years under appropriate conditions—protected from moisture, light, and air, stored refrigerated under inert atmosphere.

Applications

• Intermediate in oligosaccharide synthesis with 3-deoxy sugar residues.
• Glycosylation reactions to introduce 3-deoxy moieties.
• Medicinal chemistry for drug candidates and biochemical probes.
• Research on carbohydrate metabolism, enzyme specificity, glycosidase activity, and carbohydrate-protein interactions.

Key Characteristics

• Sugar protected by acetyl groups, easily removable.
• Enables synthesis of 3-deoxy modified carbohydrates.
• Stable under dry, dark, refrigerated storage.
• Soluble in organic solvents (chloroform, DCM, ethyl acetate).

Citation

• “Synthesis of 3-deoxy sugars”
• “Glycosylation reactions with 3-deoxy glycosyl donors”
• “Synthesis of oligosaccharides containing 3-deoxy-D-glucose (D-Tyvelose)”
• “Synthesis of carbohydrate antigens with 3-deoxy sugars”
• “Chemoenzymatic synthesis of 3-deoxy oligosaccharides”
• “Synthesis of glycosidase inhibitors with 3-deoxy sugars”
• “Bacterial polysaccharides synthesis with 3-deoxy sugars”
• “Glycoconjugates containing 3-deoxy sugars”
• “Protecting group strategies for 3-deoxy carbohydrate synthesis”
• “Tyvelose-containing oligosaccharide synthesis”