Allyl b-L-glucopyranoside

Allyl β-L-glucopyranoside is a chemically synthesized glycoside derivative of β-L-glucose where the anomeric hydroxyl is replaced by an allyl group, preserving the β-configuration of the glucopyranose ring. It appears as a white crystalline solid and serves as an important intermediate in carbohydrate chemistry, notable for its utility in synthetic glycobiology and medicinal chemistry. The allyl group is a reactive alkyne precursor allowing for bioorthogonal conjugation reactions such as copper-catalyzed azide-alkyne cycloaddition (“click” chemistry). Such reactivity facilitates selective modification and labeling of glycoconjugates and glycomimetics. The compound has a molecular formula of C12H20O6 and a molecular weight around 236.28 g/mol. It is widely applied in enzymatic glycosylation studies, molecular probe development, targeted drug delivery research, and polymer conjugation. This glycoside is supplied with high purity (≥98%), with identity confirmed by NMR and chromatographic analysis, and produced under rigorous chemical synthesis ensuring minimal microbial contamination. Proper storage refrigerated and protected from moisture and light ensures stability and a shelf life of 1–2 years.

IUPAC Name:

• Allyl β-L-glucopyranoside

Appearance:

• White to off-white crystalline powder

Source:

• Produced via chemical glycosylation of protected L-glucose derivatives with allyl alcohol under strictly controlled lab conditions

Molecular Weight and Structure:

• Molecular Formula: C12H20O6
• Molecular Weight: 236.28 g/mol
• Structure: β-L-glucopyranose ring with allyl substitution at the anomeric carbon, maintaining stereochemical integrity and unprotected hydroxyl groups
  SMILES: C=CCOC1C(C(C(C(O1)O)O)O)O

Sugar Specificity:

• Stereospecific β-L-glucoside supporting selective glycosyl donor behavior and conjugative modifications

Biological Activity:

• Primarily a synthetic intermediate and tool in chemical biology; facilitates glycan labeling, enzyme substrate analog studies, and drug carrier development; not directly pharmacologically active

Purity and Microbial Contamination:

• Purity ≥98%, confirmed by NMR, HPLC; chemical synthesis ensures negligible microbial contamination

Identity and Quality Control:

• Verified through detailed NMR (1H and 13C), mass spectrometry, chromatographic purity; batch consistency confirmed with COA and SDS documentation

Shelf Life and Storage:

• Refrigerate at 2–8 °C; protect from moisture and light; stable for 1–2 years under recommended storage

Application:

• Intermediate in selective glycosylation and conjugation reactions; key reagent for bioorthogonal labeling and glycomimetic synthesis; supports enzymatic assay development and molecular probe design in glycobiology and medicinal chemistry

Key Characteristics:

• Allyl-substituted β-L-glucopyranoside
• CAS: 85296-14-0
• Molecular weight: 236.28 g/mol
• White crystalline solid, high purity, chemically reactive
• Enables bioorthogonal chemistry and selective glycosylation
• Full analytical and quality certification provided
• Stable under controlled refrigeration
• Widely used in synthetic glycobiology and drug research

Citations:

• BLD Pharm product information
• Glentham catalog
• USBio spectral data
• Sigma-Aldrich glycoside references
• PMC chemical biology articles
• MedChemExpress probes and standards
• Synthose carbohydrate derivatives
• Patent literature on glucoside synthesis
• Benchchem reagents listing
• ScienceDirect synthetic glycochemistry reviews