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

CAS No.	58006-34-1
Synonyms	Allyl 4,6-O-benzylidene-β-L-glucopyranoside
Formula	C₁₆H₂₀O₆
Mol Weight	308.33
Packaging	Custom packs
Specification	No spec file.

Allyl 4,6-O-benzylidene-β-L-glucopyranoside is a chemically synthesized L-glucose derivative featuring a benzylidene protecting group bridging the hydroxyls at positions 4 and 6, with an allyl group substituting the anomeric hydroxyl group in the β-configuration. This white crystalline solid serves as a vital synthetic intermediate in carbohydrate chemistry and glycobiology, enabling regio- and stereoselective glycosylation reactions. The benzylidene protection introduces conformational constraint enhancing selectivity, whereas the allyl moiety acts as a versatile reactive handle for subsequent modification, including bioorthogonal conjugations such as click chemistry. With a molecular formula of C16H20O6 and molecular weight of 296.32 g/mol, this compound is primarily used in the synthesis of glycomimetics, glycoconjugates, and molecular probes for medicinal chemistry and biological studies. It is supplied with a purity of ≥98%, certified through NMR and chromatographic techniques, and produced under sterile, controlled conditions ensuring minimal microbial contamination. Proper storage under refrigerated, dry, and light-protected conditions ensures stability and a shelf life of 1–2 years, making it broadly applicable in drug discovery, molecular imaging, and glycobiology research.

IUPAC Name:

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

Synonyms:

Allyl 4,6-O-benzylidene-L-glucopyranoside
Allyl benzylidene L-glucoside
Benzylidene-protected allyl β-L-glucopyranoside

Appearance:

White crystalline powder

Source:

Obtained by chemical synthesis involving benzylidene protection of L-glucopyranose and subsequent glycosylation with allyl alcohol under anhydrous, controlled laboratory conditions

Molecular Weight and Structure:

Molecular Formula: C16H20O6
Molecular Weight: 296.32 g/mol
Structure: β-L-glucopyranoside with benzylidene acetal protecting hydroxyl groups at C4 and C6, and an allyl group attached at the anomeric center
SMILES: C=CCOC1C(C@H C@@HOC3=CC=CC=C3)O

Sugar Specificity:

β-L-glucopyranoside with selective protection facilitating regio- and stereospecific synthetic modifications

Biological Activity:

Not directly biologically active. Used as a synthetic intermediate and chemical biology tool for developing glycomimetics, drug delivery vectors, and labeled molecular probes. Supports carbohydrate-protein interaction studies and enzymatic assay development

Purity and Microbial Contamination:

Purity generally ≥98%, guaranteed by NMR and chromatographic analyses. Produced via controlled chemical synthesis ensuring synthetic-grade purity and negligible microbial contamination

Identity and Quality Control:

Confirmed by detailed NMR (1H, 13C), MS, and HPLC chromatographic purity profiles. Certificates of Analysis and Safety Data Sheets accompany the product. Melting point and specific optical rotation data are recorded for batch verification

Shelf Life and Storage:

Stored recommenced at 2–8 °C; protect from moisture, light, and heat. Stable for at least 1–2 years under specified conditions

Application:

Used as a versatile synthetic glycosyl donor and conjugation platform in oligosaccharide and glycoconjugate synthesis. Facilitates bioorthogonal labeling, medicinal and chemical biology research, drug discovery, and molecular imaging

Key Characteristics: