3,4,6-Tri-O-benzyl-2-nitro-D-galactal

3,4,6-Tri-O-benzyl-2-nitro-D-galactal is a chemically synthesized carbohydrate derivative, a modified galactose analog where hydroxyl groups at positions 3, 4, and 6 are protected by benzyl ether groups, and the 2-position bears a nitro substituent. This white crystalline solid serves as a critical intermediate in synthetic carbohydrate chemistry, particularly in the preparation of glycosyl donors and acceptors for oligosaccharide synthesis. The nitro group at C2 introduces unique reactivity that is valuable for regioselective transformations, enabling efficient glycosylation reactions and subsequent functional group modifications. Benzyl protection enhances the compound’s stability and solubility in organic solvents, facilitating purification and reaction control. This compound is employed extensively in medicinal chemistry, chemical biology, and glycobiology to probe enzyme mechanisms, develop glycomimetic agents, and synthesize structurally complex glycans. Supplied with high purity and detailed quality control data, it is stored refrigerated to maintain chemical integrity for robust use in synthetic and biological research.​

IUPAC Name

• (2R,3R,4R)-3,4-bis(phenylmethoxy)-2-nitro-2,3-dihydro-4H-pyran-2-ylmethanol derivative​

Appearance

• White crystalline powder​

Source

• Synthesized through stepwise benzyl protection and nitration of D-galactal derivatives under controlled laboratory conditions​

Molecular Weight and Structure

• Molecular Formula: C27H27NO6
• Molecular Weight: 461.51 g/mol​
• Structure: D-galactal ring with benzyl groups at 3,4,6 positions and nitro group substitution at C2; molecular complexity aids selective chemical transformations​
• SMILES: Not readily simplified, captures multiple benzyl and nitro groups characteristic of synthetic carbohydrate intermediates​

Sugar Specificity

• Galactal derivative with specific benzyl and nitro functionalization
• Utilized for synthetic manipulation in glycosyl donor and acceptor chemistry​

Biological Activity

• Primarily a synthetic intermediate with no direct biological activity
• Enables investigations into regio- and stereoselective glycosylation techniques
• Supports medicinal chemistry by serving as precursor to bioactive glycoconjugates and glycomimetics​

Purity and Microbial Contamination

• Supplied with purity ≥95%, confirmed by chromatographic methods and NMR
• Chemical synthesis ensures minimal microbial contamination​

Identity and Quality Control

• NMR, mass spectrometry, and purity by HPLC confirm identity and quality
• Melting point and spectral data documented
• Certificates of Analysis and safety data sheets provided​

Shelf Life and Storage

• Stored in a dry, cool environment, typically refrigerated at 2–8 °C
• Stable for at least 1 year under recommended storage conditions
• Protect from moisture and light to prevent degradation​

Application

• Key intermediate in carbohydrate synthesis for developing glycosyl donors/acceptors
• Enables synthesis of complex oligosaccharides and glycomimetics
• Used in medicinal chemistry for designing antitumor, antimicrobial glycoconjugates
• Supports glycosylation mechanism studies and structure-activity relationship analyses​

Key Characteristics

• Tri-O-benzyl-2-nitro modified D-galactal
• CAS number 211621-55-5
• Molecular weight 461.51 g/mol
• White crystalline solid, chemically stable
• High purity with extensive characterization
• Synthetic versatility for advanced carbohydrate chemistry
• Widely applied in glycobiology and medicinal research
• Supplied with full analytical and quality assurance documentation

Citations

• AnaxLab product data​
• ChemicalBook product details​
• CalpacLab purity and source info​
• PubChem related Galactal analogs​
• ChemPep synthesis and applications​
• Sigma-Aldrich biomarkers and reagents​
• PMC antineoplastic and antimicrobial studies​
• Thermo Scientific Chemicals catalog​
• Echemi chemical supplier data​
• Recent academic reviews on glycosylation chemistry