Allyl 4,6-O-benzylidene-β-D-glucopyranoside

Allyl 4,6-O-benzylidene-β-D-glucopyranoside is a synthesized glucose derivative in which the hydroxyl groups at the 4th and 6th positions of β-D-glucopyranose are protected via a benzylidene acetal, and the anomeric hydroxyl is substituted by an allyl group. This compound appears as a white crystalline solid and serves as an important synthetic intermediate in carbohydrate chemistry. The benzylidene group confers conformational rigidity and selective protection, improving chemical stability and facilitating regioselective reactions. The allyl group at the anomeric carbon serves as a versatile reactive moiety for subsequent modifications, such as in bioorthogonal chemistry (e.g., click reactions), glycosylation, and conjugation with biomolecules. It possesses a molecular formula of C16H20O6 and a molecular weight of about 296.32 g/mol. This intermediate is widely used in medicinal chemistry, chemical biology, and glycobiology, facilitating the production of glycomimetics, glycoconjugates, and molecular probes. It is supplied with high purity (>98%), confirmed identity, and quality control documentation, stored under refrigerated, moisture-free conditions to ensure shelf life and integrity.

IUPAC Name:

• Allyl 4,6-O-benzylidene-β-D-glucopyranoside

Synonyms:

• Allyl 4,6-O-benzylidene D-glucopyranoside
• Allyl glucopyranoside 4,6-benzylidene acetal

Appearance:

• White crystalline powder

Source:

• Synthesized via selective benzylidene acetal formation followed by glycosylation with allyl alcohol in controlled lab conditions

Molecular Weight and Structure:

• Molecular Formula: C16H20O6
• Molecular Weight: 296.32 g/mol
• Structure: Glucopyranose ring in β-configuration; benzylidene acetal bridging C4 and C6 hydroxyls; allyl group at anomeric C1
• SMILES: C=CCOC1C(COC2C=CC=CC2)OC(COC3=CC=CC3)C(O1)O

Sugar Specificity:

• A β-D-glucopyranoside derivative with benzylidene acetal providing regioselective control in synthetic chemistry
• Acts as a glycosyl donor intermediate in selective glycosylation reactions

Biological Activity:

• Serves as a synthetic intermediate without inherent bioactivity
• Enables preparation of glycoconjugates and glycomimetics
• Useful in molecular probe construction and drug delivery developments

Purity and Microbial Contamination:

• High purity ≥98%, verified via NMR and HPLC chromatography
• Chemical synthesis processes maintain microbial-free status

Identity and Quality Control:

• Full characterization conducted by NMR, MS, and chromatographic methods
• Certificates of Analysis and Safety Data Sheets provided
• Melting point and optical rotation values ensure batch uniformity

Shelf Life and Storage:

• Store in dry, sealed containers at 2–8 °C
• Protect from light and moisture to retain compound integrity
• Typical shelf life of 1–2 years under recommended conditions

Application:

• Intermediate for selective glycosylation and construction of oligosaccharides
• Facilitates synthesis of glycoconjugates for medicinal chemistry and glycobiology
• Enables bioorthogonal modifications and molecular labeling via the allyl group
• Supports enzyme mechanism studies, drug discovery, and diagnostic probe development

Key Characteristics:

• Allyl-substituted, 4,6-benzylidene protected β-D-glucopyranoside
• CAS number: 183388-21-8
• Molecular weight: 296.32 g/mol
• White crystalline, high purity compound
• Supports regio- and stereoselective synthetic approaches
• Supplied with detailed QC and batch analyses
• Stable with proper refrigerated storage
• Valuable tool in chemical biology, glycochemistry, and pharmaceutical research

Citations:

• AnaxLab product overview
• ChemicalBook reference
• Glentham Life Sciences catalog
• PubChem molecular data
• Sigma-Aldrich glycoside reagents
• PMC enzymatic and synthetic studies
• Synthose synthetic carbohydrate intermediates
• MedChemExpress bioorthogonal reagents
• Patent literature on benzylidenes
• ScienceDirect synthetic methodology articles