Ethyl a-D-glucopyranoside

Ethyl α-D-glucopyranoside is a chemically synthesized glycoside derivative of D-glucose, where the anomeric hydroxyl group is replaced by an ethyl group in the α-configuration. This compound typically appears as a white crystalline solid and serves as an important building block in carbohydrate chemistry and glycobiology. The ethyl glycoside modification confers enhanced stability compared to the reducing sugar form, making it valuable for further chemical derivatization and synthesis of oligosaccharides, glycoconjugates, and glycomimetics. It is characterized by its specificity for the α-anomer of D-glucopyranose, important in enzyme substrate studies and molecular recognition. The compound is supplied with high purity (typically ≥98%) verified by NMR and chromatographic techniques, produced under controlled conditions to minimize microbial contamination. Proper storage in a cool, dry, and dark environment extends shelf life to 1–2 years. Applications include drug design, biochemical assays, molecular labeling, and synthetic organic chemistry related to carbohydrate-based therapeutics and diagnostics.

IUPAC Name:

Ethyl 2,3,4,6-tetra-OH-α-D-glucopyranoside​

Synonyms:

• Ethyl α-D-glucopyranoside
• α-D-Glucopyranosyl ethyl ether
• 2,3,4,6-Tetrahydroxyethyl α-D-glucopyranoside​

Appearance:

• White to off-white crystalline powder​

Source:

• Chemically synthesized from D-glucose by acid-catalyzed glycosylation with ethanol under controlled laboratory conditions​

Molecular Weight and Structure:

• Molecular formula: C8H16O6
• Molecular weight: 208.21 g/mol​
• Structure: α-D-glucopyranose ring with the anomeric hydroxyl replaced by an ethyl group; four free hydroxyl groups at C2, C3, C4, C6​
  SMILES: CCOC1C(C(C(C(O1)O)O)O)O​

Sugar Specificity:

• Specific α-anomer of D-glucopyranoside, widely studied for its enzyme-substrate interactions and molecular recognition​

Biological Activity:

• Mainly a stable synthetic intermediate; utilized as a substrate analog in enzymatic studies, glycomimetic synthesis, and molecular probe development; intrinsic biological activity limited​

Purity and Microbial Contamination:

• Purity typically ≥98%, confirmed with NMR and chromatographic methods; synthesized with high-quality protocols minimizing microbial contamination​

Identity and Quality Control:

• Verified by NMR (1H,13C), MS, and HPLC purity profiles; accompanied by Certificates of Analysis and SDS; melting point and optical rotation data supplied for QC​

Shelf Life and Storage:

• Store sealed at 2–8 °C, protected from moisture and light; shelf life 1–2 years under proper storage conditions​

Application:

• Used as a glycosyl donor in synthetic oligosaccharide and glycoconjugate synthesis; facilitates drug discovery and glycobiology research; employed in labeling and molecular probe design; supports enzymatic and chemical glycosylation studies​

Key Characteristics:

• Ethyl glycoside of α-D-glucopyranose
• CAS: 3010-03-7
• Molecular weight: 208.21 g/mol
• White crystalline powder, high purity and chemical stability
• Supports regio- and stereoselective glycosylation reactions
• Supplied with comprehensive analytic and quality documentation
• Stable under refrigerated, dry storage conditions
• Widely used in synthetic and medicinal carbohydrate chemistry

Citations:

• AnaxLab product details​
• CalpacLab chemical info​
• TCIChemicals supplier data​
• Sigma-Aldrich related glycoside references​
• PubChem molecular and chemical data​
• PMC carbohydrate research papers​
• MedChemExpress chemical standards
• Synthose glycosylation intermediates
• Patent literature on ethyl glycosides​
• ScienceDirect carbohydrate synthesis reviews​