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

1,2,3,4-Tetra-O-acetyl-6-deoxy-D-glucopyranose is a synthetically-derived, acetyl-protected sugar crucial to modern carbohydrate chemistry and glycoscience research. This compound is used as a building block in the synthesis of complex oligosaccharides, glycoconjugates, and glycosides, enabling precise manipulation of carbohydrate structures for both research and biomedical applications. The acetylation of its four hydroxyl groups at positions 1, 2, 3, and 4 provides selective protection and facilitates controlled chemical reactions. The molecule is not naturally occurring and is obtained by chemical modification of D-glucose, specifically through deoxygenation at the 6-position and targeted acetylation.

IUPAC Name:

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

Appearance:

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

Source:

• Synthesized from D-glucose or similar precursors via multistep reactions involving deoxygenation and acetyl protection; not present in natural sources.

Molecular Weight and Structure:

• Molecular weight: 332.30 g/mol.
• Molecular formula: C14H20O9.
• Structure: Features a six-membered pyranose ring with acetylation at positions 1–4 and a deoxy group at position 6; exists as α or β anomer depending on the configuration.

Sugar Specificity:

• Acts as a glycosyl donor with D-glucose backbone specificity; incorporated into diverse oligosaccharide chains for targeted glycosylation.

Biological Activity:

• Not inherently bioactive; its value is as a protected sugar intermediate in the synthesis of biologically active glycosides, conjugates, and carbohydrate-based drugs. Final biological properties are determined after deprotection or incorporation in bioactive compounds.

Purity and Microbial Contamination:

• Purity: Typically ≥98% by ^1H-NMR or HPLC.
• Microbial contamination: Not usually of concern (chemical context), but monitored for biological applications to ensure suitability as a reagent.

Identity and Quality Control:

• Identity confirmed by ^1H/^13C-NMR, mass spectrometry, and melting point (183-184°C).
• Quality control includes purity assay, water content (Karl Fischer titration), and absence of significant process impurities.

Shelf Life and Storage:

• Store at 0 to –20°C, dry and protected from light.
• Stable for over two years under ideal conditions; shipping at ambient temperature is typically acceptable.

Application:

• Intermediate in oligosaccharide and glycoconjugate synthesis for targeted glycosylation reactions and structural diversity.
• Used in medicinal chemistry for drug design and in biochemical studies for carbohydrate metabolism research.

Key Characteristics:

• Protected sugar facilitating selective synthesis.
• Soluble in organic solvents (e.g., DCM, chloroform, ethyl acetate).
• Enables controlled introduction and removal of functional groups.
• Essential building block for automated, solid-phase, and solution-phase glycosylation.

Citation 

• Product page, identity, and purity data
• Technical properties, storage, regulatory info
• Application and carbohydrate research context
• IUPAC name and structure data
• Synthesis and building block details
• Analytical confirmation and melting point
• Glycosylation and oligosaccharide synthesis
• Biological activity context
• Purity analysis and QA methods
• Storage life and chemical stability