1,2,3,4-Tetra-O-acetyl-α-L-fucopyranose

1,2,3,4-Tetra-O-acetyl-α-L-fucopyranose

1,2,3,4-Tetra-O-acetyl-α-L-fucopyranose (CAS: 24332-95-4) is a purified, acetyl-protected derivative of L-fucose, widely employed as a versatile intermediate in carbohydrate, pharmaceutical, biochemical, and diagnostics research.chemicalbook+2

Chemical Properties

• Molecular Formula: C₁₄H₂₀O₉sigmaaldrich+2

• Molecular Weight: 332.30 g/molchemicalbook+1

• Appearance: White to colourless crystalline solid or thick syrup, depending on purity and supplier.pharmaffiliates+1

• Purity: >98% (HPLC analysis for research grade).tcichemicals+1

• Melting Point: 90–96 °C.tcichemicals+1

• Specific Rotation: Approximately –118° to –125° (C=1, CHCl₃).sigmaaldrich+1

• Solubility: Sparingly soluble in acetone, dichloromethane, and chloroform; slightly soluble in methanol.chemicalbook

• Storage: Recommended 2–8 °C; avoid heat and moisture for long-term stability.pharmaffiliates+1

Structure and Synonyms

• IUPAC Name: [(2S,3R,4R,5S,6S)-4,5,6-triacetyloxy-2-methyloxan-3-yl] acetatepubchem.ncbi.nlm.nih

• SMILES: C[C@@H]1OC@@HC@@HC@H[C@@H]1OC(C)=Osigmaaldrich

• Other Synonyms: 1,2,3,4-Tetra-O-acetyl-L-fucose, L-Fucose tetraacetate, 1,2,3,4-Tetraacetate-6-deoxy-L-galactopyranose.tcichemicals+2

Key Applications

• Glycobiology: Used as a precursor for the synthesis of oligosaccharides, glycosyl donors, and as a glycan building block in studies of cell-surface carbohydrates.chemimpex+1

• Pharmaceuticals: Supports the creation of drug delivery systems and bioconjugates through improved stability, solubility, and reactivity.chemimpex

• Food/Cosmetics: Used in advanced product formulations to enhance stability, flavor, preservation, and moisturizing properties.chemimpex

• Biotechnology: Key reagent for diagnostic assay development, particularly in antigen and antibody research.bocsci

Safety/Handling

• Non-hazardous, may be heat sensitive—handle under ambient or refrigerated conditions.pharmaffiliates+1

This compound is essential for synthetic carbohydrate chemistry, offering robust protection for the hydroxyls on fucose during complex molecule assembly and enabling precise bioconjugation for advanced biomedical research.bocsci+2