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

Allyl 4,6-O-benzylidene-α-D-glucopyranoside is a chemically synthesized glucose derivative where the hydroxyl groups at positions 4 and 6 are protected by a benzylidene acetal, and the anomeric hydroxyl is substituted with an allyl group. This white crystalline solid provides enhanced stability and reactivity for synthetic carbohydrate chemistry applications. The benzylidene protection imposes conformational rigidity and selective reactivity, while the allyl group at the anomeric position serves as a versatile reactive handle useful in glycosylation and further functionalization. It has a molecular formula of C16H20O6 and a molecular weight of approximately 296.32 g/mol. Allyl 4,6-O-benzylidene-α-D-glucopyranoside is a key intermediate in the synthesis of complex oligosaccharides, glycoconjugates, and glycomimetics, and is critical for medicinal chemistry, chemical biology, and glycobiology research. It is supplied with high purity and validated identity, requiring storage under refrigerated, moisture-free conditions to maintain a stable shelf life. The compound is widely applied in drug design, enzymatic studies, targeted delivery systems, and biomolecular labeling.

IUPAC Name

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

Appearance

• White crystalline powder

Source

• Synthetically prepared by selective benzylidene acetal formation and allylation of glucose derivatives in controlled chemical synthesis environments

Molecular Weight and Structure

• Molecular Formula: C16H20O6
• Molecular Weight: 296.32 g/mol
• Structure: α-D-glucopyranoside with a benzylidene acetal protecting groups bridging C4 and C6 hydroxyls, and an allyl group replacing the anomeric hydroxyl
• SMILES: C=CCOC1C(COC2=CC=CC=C2)OC(COC3=CC=CC=C3)C(O1)O

Sugar Specificity

• Derivative of α-D-glucopyranoside with protective modifications for selective synthetic utility
• Used in regio- and stereospecific glycosylation reactions

Biological Activity

• Functions primarily as a synthetic intermediate with no direct intrinsic bioactivity
• Facilitates targeted drug delivery system design and chemical biology research
• Used in enzymatic reaction studies and glycan labeling

Purity and Microbial Contamination

• Purity ≥ 98%, validated by NMR, HPLC, and chromatographic techniques
• Chemical synthesis and processing ensure minimal microbial contamination

Identity and Quality Control

• Confirmed identity via 1H-NMR, 13C-NMR, mass spectroscopy, and HPLC chromatograms
• Certificates of Analysis and Safety Data Sheets provide analytical verification
• Melting point and optical rotation data available for batch consistency

Shelf Life and Storage

• Store tightly sealed in a dry, cool place at 2–8 °C
• Stable for 1–2 years under recommended storage conditions
• Protect from light, moisture, and heat to maintain integrity

Application

• Key intermediate in oligosaccharide and glycoconjugate synthesis
• Enables bioorthogonal conjugation and molecular probe development via the allyl group
• Used in medicinal chemistry for drug delivery, enzymatic assay design, and glycobiology research

Key Characteristics

• Allyl-protected α-D-glucopyranoside with benzylidene acetal at C4,C6
• CAS number: 20746-64-9
• Molecular weight: 296.32 g/mol
• White, crystalline, high-purity solid supportive of synthetic versatility
• Essential for regioselective glycosylation and molecular labeling
• Supplied with full analytical verification and COA
• Stable under refrigerated, dry conditions for prolonged usage

Citations

• ChemicalBook detailed profile
• Glentham Life Sciences catalog
• LookChem supplier details
• PubChem structural data
• Sigma-Aldrich glycoside reagents
• PMC enzymology and chemical biology papers
• Synthose glycosylation intermediates
• MedChemExpress chemical standards
• Recent carbohydrate synthesis reviews
• Patent documents on glycosylation chemistry