D-Galactal

D-Galactal is a chemically synthesized unsaturated sugar derivative derived from D-galactose where the anomeric carbon (C1) is part of an alkene, forming a glycal. It appears as a white crystalline solid and is a key intermediate in carbohydrate chemistry, valued for its reactive double bond that facilitates selective addition and glycosylation reactions. This unsaturation at the anomeric position allows D-galactal to act as a glycosyl donor for constructing diverse oligosaccharides and glycoconjugates with controlled regio- and stereochemistry. It is widely used in chemical biology, synthetic organic chemistry, and medicinal chemistry for synthesizing complex carbohydrate structures and glycomimetics. The compound is supplied with a high purity grade and stringent quality assurance. Preservation under refrigerated conditions ensures stability and shelf life, supporting its applications in pharmaceutical development, enzymatic mechanism studies, and drug discovery involving carbohydrate-based interventions.

IUPAC Name

• (2R,3R,4S,5R)-3,4,5-trihydroxy-2,3-dihydro-4H-pyran-2-ylidene

Appearance

• White crystalline powder

Source

• Prepared by chemical dehydration and functional group manipulation of D-galactose in laboratory settings

Molecular Weight and Structure

• Molecular Formula: C6H10O5
• Molecular Weight: 162.14 g/mol
• Structure: Six-membered pyran ring featuring a double bond between C1 and C2 (glycal form), retaining hydroxyl groups at C3, C4, and C5
• SMILES: C1=COC(C(O)C(O)CO)O1

Sugar Specificity

• Glycal derivative of D-galactose with anomeric unsaturation
• Acts as an electrophilic glycosyl donor in selective carbohydrate synthesis

Biological Activity

• Primarily a chemical intermediate with research utility in enzymatic and chemical glycosylation
• Facilitates structure-function studies of glycosyltransferases and glycosidases
• Supports synthesis of glycomimetics and carbohydrate-based drugs

Purity and Microbial Contamination

• Purity of ≥95% ensured by NMR, HPLC, and chromatographic analyses
• Synthesized in sterile chemical environments minimizing microbial contamination risks

Identity and Quality Control

• Verified identity through NMR and mass spectrometry
• Certificate of Analysis and Safety Data Sheets accompany each batch
• Melting point and spectral data provided for quality validation

Shelf Life and Storage

• Store in sealed containers at 2–8 °C
• Stability typically exceeds one year if protected from moisture and light
• Recommend dry, cool, and dark conditions to prevent degradation

Application

• Used as a glycosyl donor in stereoselective synthesis of oligosaccharides
• Intermediate for constructing glycoconjugates and glycomimetic molecules in medicinal chemistry
• Supports enzymatic glycosylation studies and biochemical probe development
• Employed in drug discovery and molecular imaging involving carbohydrate structures

Key Characteristics

• D-galactal glycal with anomeric double bond
• CAS number 77944-14-2
• Molecular weight 162.14 g/mol
• White crystalline solid of high purity and stability
• Chemical precursor for synthesis of complex carbohydrates
• Supplied with full quality control documentation
• Crucial for synthetic, enzymatic, and medicinal chemistry
• Enables regio- and stereoselective glycosylation reactions

Citations

• AnaxLab chemical info
• PubChem glycal compound data
• BLD Pharm catalog
• Sigma-Aldrich carbohydrate chemicals
• PMC enzymology studies on glycals
• Echemi supplier data
• Chemistry Europe glycoside synthesis reviews
• Synthose synthetic carbohydrate kit listings
• Glentham Life Sciences glycosyl donor
• Patent literature on glycal chemistry