β-D-ribopyranose 1,2,3,4-Tetraacetate

β-D-Ribopyranose 1,2,3,4-Tetraacetate

β-D-Ribopyranose 1,2,3,4-Tetraacetate (CAS No. 4049-34-7) is a protected ribose derivative widely used in organic synthesis and biochemistry. Below is a detailed description based on its chemical properties, applications, and safety guidelines:

Chemical Identification

• CAS Registry Number: [4049-34-7]
• MDL Number: MFCD00006596[User Data]
• Catalog Number: A873321 (97% purity)[User Data]
• Molecular Formula: C13H18O9\text{C}_{13}\text{H}_{18}\text{O}_9C13H18O9
• Molecular Weight: 318.28 g/mol
• IUPAC Name: [(3R,4R,5R,6S)-4,5,6-Triacetyloxyoxan-3-yl] acetate
• Synonyms:
  • Tetra-O-acetyl-β-D-ribopyranose
  • NSC 116266
  • EINECS 223-750-2

Physical Properties

Chemical Properties

• Solubility: Soluble in organic solvents (e.g., DMSO, chloroform) and partially soluble in water.
• Stability: Stable under standard conditions but sensitive to hydrolysis.
• Functional Groups: Four acetyl groups protect hydroxyl groups, enabling controlled deprotection during synthesis.

Applications

1. Pharmaceutical Research:
   • Key intermediate in synthesizing nucleoside analogs and antiviral/anticancer drugs
   • Used to study RNA structures and enzymatic processes (e.g., replication, transcription).
2. Biotechnology:
   • Critical for RNA-based vaccine development and gene therapy.
3. Food Industry:
   • Acts as a flavoring agent or sweetener due to sugar-like properties.
4. Cosmetics:
   • Enhances moisturizing properties in skincare formulations.
5. Material Science:
   • Explored for modifying carbohydrate-based polymers.

Safety and Handling

• Hazards: May cause skin/eye irritation. Avoid inhalation or direct contact.
• Precautions:
  • Use PPE (gloves, goggles) in a well-ventilated area.
  • Store in a cool, dry place away from moisture.

Key Notes

• Regulatory Status: Listed in chemical databases (e.g., PubChem, EINECS) for research use.
• Synthesis Utility: Acetyl groups enable selective functionalization, making it indispensable for nucleic acid chemistry.

Meta Description

β-D-Ribopyranose 1,2,3,4-Tetraacetate (CAS 4049-34-7) is a vital reagent in nucleic acid synthesis, drug development, and biotechnology. With 97% purity and a melting point of 109–113 °C, this acetyl-protected ribose derivative enables precise chemical modifications for RNA research and industrial applications.

Citations:

1. https://www.chemimpex.com/products/32359
2. https://www.scbt.com/p/beta-d-ribopyranose-1-2-3-4-tetraacetate-4049-34-7
3. https://pubchem.ncbi.nlm.nih.gov/compound/Tetra-O-acetyl-beta-D-ribopyranose
4. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3161757.htm
5. https://www.chembk.com/en/chem/Beta-D-Riboyranose%201,2,3,4-Tetraacetae
6. https://www.lookchem.com/sds4049-34-7.html
7. https://www.tcichemicals.com/IN/en/p/R0065
8. https://cymitquimica.com/products/IN-DA003BP0/4049-34-7/d-ribopyranose-1234-tetraacetate/