1,2;3,4-Di-O-isopropylidene-α-D-fucopyranose

1,2;3,4-Di-O-isopropylidene-α-D-fucopyranose is a synthetic derivative of the deoxy sugar fucose, a monosaccharide commonly found in mammalian glycoconjugates and bacterial polysaccharides. The term “di-O-isopropylidene” indicates that two isopropylidene protecting groups are attached to the fucose molecule. Specifically, one isopropylidene group protects the hydroxyl groups at positions 1 and 2, forming a cyclic ketal, and another protects the hydroxyl groups at positions 3 and 4, also forming a cyclic ketal. These protecting groups are employed to selectively block the reactivity of these hydroxyls, allowing for controlled chemical modifications at the remaining position, which is typically at C-6 (the methyl group) or after selective deprotection. This compound is valuable in the synthesis of more complex fucosylated oligosaccharides, glycoconjugates, and other fucose-containing molecules, where the controlled introduction of fucose is essential. It serves as a versatile building block for constructing diverse carbohydrate structures with defined linkages and biological activities.

IUPAC Name 

• IUPAC Name: (3aR,6R,6aR)-5-((4R,5R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d]dioxole

Appearance

• Typically colorless to white crystalline solid or powder

Source

• Synthetically derived
• Prepared through chemical reactions starting from fucose
• Protection of hydroxyl groups at positions 1,2 and 3,4 via isopropylidene groups under acidic conditions

Molecular Weight and Structure

• Molecular Weight: 244.28 g/mol
• Molecular Formula: C12H20O5
• Structure: Six-membered fucose ring (6-deoxy sugar)
• Two isopropylidene groups form cyclic ketals at positions 1,2 and 3,4
• Anomeric carbon (C1) locked in α configuration

Sugar Specificity

• No inherent biological sugar-binding specificity as a protected derivative
• Specificity arises when incorporated into complex fucosylated molecules

Biological Activity

• Compound itself inactive biologically
• Biological roles depend on incorporated fucosylated molecules
• Fucose residues involved in cell-cell recognition, immune response, and signaling

Purity and Microbial Contamination

• High purity essential for chemical synthesis
• Purity assessed by HPLC, TLC, GC, and NMR spectroscopy
• Microbial contamination generally not a concern for chemical use
• Sterility testing required if used for biological studies

Identity and Quality Control

• Confirmed by ^1H and ^13C NMR spectroscopy
• Mass spectrometry used for structure confirmation
• Optical rotation and melting point measurements for QC
• Water content determined by Karl Fischer titration

Shelf Life and Storage

• Several years’ stability if protected from moisture, light, and air
• Stored under inert atmosphere at refrigerated temperatures

Application

• Intermediate in synthesis of fucosylated oligosaccharides
• Used to introduce fucose residues into glycoconjugates (glycoproteins, glycolipids)
• Important in carbohydrate-protein interaction studies
• Utilized in medicinal chemistry for drug discovery targeting fucose-binding proteins

Key Characteristics

• Protected fucose with isopropylidene groups
• Versatile for controlled fucosylation reactions
• Stable under proper storage conditions
• Soluble in chloroform, dichloromethane, ethyl acetate
• Locked α-anomeric configuration

Citation

• Product and application overview — Chem-Impex
  https://www.chemimpex.com/products/28165
• Compound entry and properties — PubChem
  https://pubchem.ncbi.nlm.nih.gov/compound/10977680
• Usage and synthesis details — ChemicalBook
  https://www.chemicalbook.com/ProductChemicalPropertiesCB1311963_EN.htm
• Enzyme substrate synthesis information — ChemDad
  https://chemdad.com/index.php?c=article&id=14646
• Protected intermediate in glycoconjugate synthesis — Atomfair
  https://atomfair.com/product/atomfair-1234-di-o-isopropylidene-alpha-d-fucopyranose-c12h20o5-cas-4026-27-1/
• General glycosylation procedure involving isopropylidene sugars — ACS Publications
  https://pubs.acs.org/doi/10.1021/acs.joc.8b02613
• Fucosylated antigen synthesis in cancer research — PMC NIH
  https://pmc.ncbi.nlm.nih.gov/articles/PMC298681/
• Fluorinated fucose analogs in cancer proliferation inhibition — PMC NIH
  https://pmc.ncbi.nlm.nih.gov/articles/PMC10901565/
• Lewis antigen biosynthesis structural basis — PMC NIH
  https://pmc.ncbi.nlm.nih.gov/articles/PMC10726971/
• Glycoengineering and E-selectin ligand studies — PubMed
  https://pubmed.ncbi.nlm.nih.gov/27335219/