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

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

3,4-Di-O-acetyl-L-fucal (CAS: 54621-94-2) is a specialized glycal derivative used as an intermediate in carbohydrate chemistry, particularly for the stereoselective synthesis of glycosides and related complex molecules.caymanchem+1

Chemical Identity and Structure

• IUPAC Name: (2S,3R,4S)-4-Acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl acetatesynthose+1
• Chemical Formula: C10H14O5C_{10}H_{14}O_5C10H14O5chemicalbook+2
• Molecular Weight: 214.22 g/molchemscene+2
• Synonyms: L-Fucal diacetate, 3,4-Diacetyl-L-fucal, 3,4-di-O-acetyl-2,6-anhydro-1,5-dideoxy-L-arabino-hex-5-enitolsigmaaldrich+1

• Structure Descriptors:

• SMILES: C(C)(=O)O[C@@H]1C@@HCsynthose
• InChI: InChI=1S/C10H14O5/c1-6-10(15-8(3)12)9(4-5-13-6)14-7(2)11/h4-6,9-10H,1-3H3/t6-,9-,10+/m0/s1sigmaaldrich+1
• InChI Key: NDEGMKQAZZBNBB-JMOVZRAMSA-Nsynthose+1

Physical and Chemical Properties

• Appearance: White crystalline solidglentham+2
• Purity: ≥95% (commonly NMR validated)nordicbiosite+2
• Melting Point: 46–48°Cglentham+1
• Solubility: Soluble in DCM (dichloromethane), DMF (dimethylformamide), DMSO (dimethyl sulfoxide), ethyl acetate, methanol; poorly soluble in water due to increased hydrophobicity from acetylationcymitquimica+2
• Storage: Store at 0 to −20°C; recommended storage is in tightly sealed containers to avoid moisture and repeated freeze-thaw cyclesglpbio+1

Chemical Role and Applications

• Role: Glycal precursor useful in advanced carbohydrate synthesis. Its acetyl-protected hydroxyls confer stability and modify reactivity, making it ideal for developing stereoselective glycosylation reactions.caymanchem+1
• Synthetic Utility:
• Used in palladium-catalyzed stereoselective glycoside synthesis.glpbio+1
• Precursor for copper-catalyzed synthesis of 2-deoxyglycosides.glpbio
• Intermediate for preparing glycosides, oligosaccharides, and in glycoprotein synthesis studies.cymitquimica
• Biological Relevance: Fucose-derivatives are relevant in cell signaling, glycoprotein function, and can be investigated for biological activity due to the important role of fucose in biochemistry.cymitquimica

Safety and Handling

• GHS Classification: Not considered hazardous according to GHS standards, though proper laboratory practice should always be observed.synthose
• Hazard Statements: Some sources indicate H302, H315, H319, H335; check up-to-date SDS for operational safety.sigmaaldrich

Regulatory and Documentation

• CAS Registry: 54621-94-2chemicalbook+1
• Product Documentation: SDS and Certificate of Analysis available from suppliers.nordicbiosite+2
• Transport/Export: Ambient shipping; US tariff code: 2940006000.synthose

Summary Table

3,4-Di-O-acetyl-L-fucal is an important intermediate for advanced carbohydrate chemistry, prized for its stability, reactivity, and utility in stereoselective syntheses.caymanchem+3