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D-Arabinonic Acid, 2-C-Methyl-4,5-O-(1-Methylethylidene)-, Ethyl Ester (CAS No. 93635-76-8) is a specialized organic compound utilized primarily in pharmaceutical intermediates and synthetic chemistry. Its structural complexity and reactivity make it valuable in the development of advanced therapeutics and chiral building blocks.

1. Pharmaceutical Intermediates

• Key Intermediate in Antiviral Drug Synthesis:
  This compound serves as a critical intermediate in the synthesis of sofosbuvir, a nucleotide analog used to treat hepatitis C virus (HCV) infections. Its role involves the formation of protected sugar moieties essential for the drug’s antiviral activity.

• Chiral Synthesis:
  The stereochemistry of the molecule (2-C-methyl substitution and 4,5-O-isopropylidene protection) enables the asymmetric synthesis of enantiomerically pure compounds, which are crucial in pharmaceuticals to avoid adverse drug reactions and enhance efficacy.

2. Organic Synthesis and Research

• Protecting Group for Carbohydrates:
  The 4,5-O-isopropylidene (acetonide) protection is widely employed in carbohydrate chemistry to shield reactive hydroxyl groups during glycosylation reactions. This allows for selective modification of other functionalities without unwanted side reactions.

• Synthetic Building Block:
  The compound acts as a precursor for the synthesis of modified sugars, nucleosides, and glycomimetics. Its ethyl ester functionality can be hydrolyzed to generate the corresponding carboxylic acid, facilitating further transformations.

3. Biochemical and Enzymatic Studies

• Enzyme Inhibitors:
  Derivatives of this compound have been explored as inhibitors of glycosyltransferases and other carbohydrate-processing enzymes, aiding in the study of glycan biosynthesis and potential therapeutic targeting.

• Prodrug Development:
  The ethyl ester group can be utilized in prodrug design, where enzymatic hydrolysis in vivo releases the active parent compound, improving bioavailability and pharmacokinetic properties.

4. Material Science Applications

• Chiral Ligands:
  The stereochemistry of the molecule makes it suitable for use as a chiral ligand in asymmetric catalysis, contributing to the development of enantioselective synthetic methodologies.

• Polymer Chemistry:
  Though less common, the compound’s functional groups could potentially be incorporated into polymers for applications in drug delivery or materials with tailored properties.

Handling and Safety Considerations

• Reactivity:
  The compound should be handled under inert atmospheric conditions to avoid hydrolysis of the acetonide group.
• Storage:
  It should be stored in a cool, dry place, away from moisture and strong acids/bases to prevent degradation.
• Safety:
  As with many organic chemicals, appropriate personal protective equipment (PPE) should be used, and safety data sheets (SDS) must be consulted for specific handling guidelines.