1-(2-Propynyl) 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside

1-(2-Propynyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside is a chemically synthesized derivative of β-D-glucopyranose where the anomeric hydroxyl group is substituted with a 2-propynyl group (an alkyne), and the remaining hydroxyl groups at positions 2, 3, 4, and 6 are protected by acetylation. This compound is a white crystalline solid that serves as an important intermediate in carbohydrate chemistry, especially in bio-orthogonal click chemistry and glycoconjugate synthesis. The 2-propynyl group provides a reactive alkyne handle that facilitates selective conjugation reactions, such as copper-catalyzed azide-alkyne cycloaddition, enabling targeted labeling and functionalization. The acetyl protections enhance stability and solubility in organic solvents, allowing controlled and regioselective glycosylation. This compound is widely employed in medicinal chemistry, molecular biology, and chemical biology for drug design, biomolecular labeling, and synthesis of glycomimetics. It is supplied with high purity and comprehensive quality controls, stored under refrigerated conditions to ensure shelf life and stability.

IUPAC Name

• 1-(Prop-2-yn-1-yl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Appearance

• White crystalline powder

Source

• Synthesized by selective alkynylation and acetylation of β-D-glucopyranose derivatives under laboratory conditions

Molecular Weight and Structure

• Molecular Formula: C16H20O9
• Molecular Weight: 356.32 g/mol
• Structure: Acetylated β-D-glucopyranoside with a propargyl (2-propynyl) substituent at the anomeric position, featuring acetyl protections at C2, C3, C4, and C6
• SMILES: CC(=O)O[C@H]1OC@HC@@HC@H[C@H]1OC(C)=O

Sugar Specificity

• β-D-glucopyranoside derivative with an alkyne functional group enabling bioorthogonal chemistry
• Used as a glycosyl donor and reactive handle for conjugation chemistry

Biological Activity

• Mainly a synthetic intermediate, enabling site-specific labeling and conjugation of biomolecules
• Facilitates development of probes and therapeutics targeting carbohydrate-mediated pathways
• Important in drug delivery system design and molecular imaging

Purity and Microbial Contamination

• Purity typically ≥98%, verified by NMR and HPLC methods
• Synthesized under rigorous, sterile chemical synthesis conditions, reducing microbial contamination risk

Identity and Quality Control

• Verified by 1H, 13C NMR, MS, and chromatographic purity profiles
• Certificates of Analysis and Safety Data Sheets supplied
• Melting point and optical rotation values documented for quality assurance

Shelf Life and Storage

• Store sealed under refrigeration (2–8 °C), protected from moisture and light
• Stable for 1–2 years under recommended conditions
• Avoid exposure to heat and humidity

Application

• Utilized as a versatile glycosyl donor and alkyne-bearing entity for click chemistry
• Enables synthesis of glycomimetics, glycoconjugates, and bioconjugation probes
• Used in medicinal chemistry and glycobiology for drug discovery and molecular labeling
• Supports targeted imaging and therapeutic agent development

Key Characteristics

• Alkynylated and tetra-O-acetylated β-D-glucopyranoside
• CAS number: 1073127-14-2
• Molecular weight: 356.32 g/mol
• White crystalline solid with high purity and well-characterized structure
• Importance in bio-orthogonal chemistry and synthetic glycobiology
• Provides reactive alkyne handle for selective conjugation
• Sold with full analytical and quality assurance documentation
• Stable intermediate for advanced synthetic and biological applications

Citations

• AnaxLab chemical data
• ChemicalBook compound information
• PubChem spectral and molecular data
• Sigma-Aldrich glycoconjugate reagents
• PMC articles on click chemistry and glycobiology
• ScienceDirect synthetic carbohydrate chemistry
• MedChemExpress glycosylation intermediates
• Patent literature on glycoconjugates
• Glentham Life Sciences product profile
• Chemistry Europe reviews on bioorthogonal handles