3,4-Di-O-acetyl-D-fucal

3,4-Di-O-acetyl-D-fucal is a chemically synthesized carbohydrate derivative, specifically a glycal precursor used in carbohydrate and glycoside synthesis. It is derived from fucose by acetylation of the hydroxyl groups at positions 3 and 4, and features a double bond in the sugar ring characteristic of glycals. This compound serves as a versatile intermediate for stereoselective synthesis of glycosides and related derivatives, aiding research in glycoscience and medicinal chemistry. It facilitates the formation of 2-deoxyglycosides in palladium- or copper-catalyzed reactions, allowing the construction of complex sugar molecules with high specificity. Due to its role as a synthetic building block, it is widely used in biochemical, pharmaceutical, and organic synthesis research to study carbohydrate interactions, structure-activity relationships, and to develop novel therapeutics. It appears as a white crystalline solid with high purity, and is supplied under strict quality control for research applications.​

IUPAC Name

• (2S,3R,4S)-4-Acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl acetate​

Appearance

• White crystalline solid​

Source

• Chemically synthesized from fucose derivatives through selective acetylation and elimination reactions​

Molecular Weight and Structure

• Molecular formula: C10H14O5​
• Molecular weight: 214.22 g/mol​
• Structure: Glycal with di-O-acetyl groups at positions 3 and 4, featuring a pyranose ring with a double bond (unsaturation)​
• SMILES: CC(O[C@@H]1C@HC@HOC=C1)=O​

Sugar Specificity

• Specific to fucose analog pathway as a glycal derivative
• Acts as a glycosyl donor precursor in synthesis of deoxyglycosides​

Biological Activity

• Used primarily as a synthetic intermediate rather than a bioactive compound
• Indirectly supports biological research by enabling synthesis of bioactive glycosides and pharmaceuticals​

Purity and Microbial Contamination

• Purity ≥95% confirmed by 1H-NMR or HPLC​
• Typically free from microbial contamination owing to chemical synthesis and high purity standards​

Identity and Quality Control

• Verified by NMR spectroscopy, HPLC, and mass spectrometry
• Supplied with Certificates of Analysis confirming chemical identity and purity
• Melting point generally reported around 46-48°C​

Shelf Life and Storage

• Store at -20°C to maintain stability
• Stable for 1 year or more under recommended storage conditions
• Protect from light and moisture, avoid repeated freeze-thaw cycles​

Application

• Key precursor in palladium- and copper-catalyzed stereoselective synthesis of 2-deoxyglycosides
• Widely used in carbohydrate chemistry, glycoside synthesis, and medicinal chemistry research
• Supports development of novel carbohydrate-based drugs and biochemical tools​

Key Characteristics

• Glycal derivative with acetyl groups at 3 and 4 positions on D-fucal
• CAS number 54621-94-2
• White crystalline solid with molecular weight 214.22 g/mol
• High purity ≥95%, with strict quality control measures
• Essential intermediate for stereoselective glycosylation reactions
• Stable under -20°C storage for extended shelf life
• Supports synthesis of bioactive glycosides and drug candidates
• Integral to carbohydrate synthetic chemistry and glycoscience research
• Used as a starting material for synthesis of 2-deoxyglycosides via metal-catalysis
• Enables precise control over stereochemistry in glycosylation

Citation 

• Cayman Chemical: 3,4-Di-O-acetyl-L-fucal​
• Synthose product sheet 54621-94-2​
• ChemicalBook datasheet​
• GLPbio chemical properties​
• AABlocks catalog​
• PubMed article on glycal applications​
• ACS Publications on synthesis​
• Sigma-Aldrich related glycal products​
• MedChem Express glycal precursor​
• Glentham Life Sciences product listing​