1,2,3,5-Tetra-O-acetyl-α-D-arabinofuranose

1,2,3,5-Tetra-O-acetyl-α-D-arabinofuranose

1,2,3,5-Tetra-O-acetyl-α-D-arabinofuranose is a chemically modified sugar derivative that plays a significant role in organic chemistry and carbohydrate synthesis. Below is a comprehensive overview of its properties, structure, and applications.

Chemical Identity

• CAS Number: 43225-70-3
• Product Code: A1251150
• IUPAC Name: [(2R,3R,4S,5R)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.28 g/mol

Physical Properties

• Appearance: Colorless to off-white oil or semi-solid
• Purity: ≥95% (typically confirmed via ¹H-NMR)
• Boiling Point: 140 °C at 0.01 mmHg
• Density: 1.31 g/mL at 25 °C
• Refractive Index: n20/D 1.4500
• Solubility: Slightly soluble in chloroform and ethyl acetate; slightly soluble in methanol.

Structural Features

This compound features:

• A β-D-arabinofuranose backbone with acetyl groups at the 1, 2, 3, and 5 positions.
• The acetylation enhances the stability of the molecule and facilitates further chemical reactions.
• Retention of the α-anomeric configuration is crucial for its reactivity in glycosylation processes.

Applications

1,2,3,5-Tetra-O-acetyl-α-D-arabinofuranose is utilized in various fields:

• Organic Synthesis: Acts as a protected intermediate in the synthesis of glycosides and other carbohydrate derivatives.
• Pharmaceutical Research: Used to develop glycosidase inhibitors and other bioactive compounds.
• Biochemical Studies: Employed in research involving carbohydrate-protein interactions and enzymatic mechanisms.

Safety and Handling

• Hazard Statements: Classified as dangerous with risk of serious eye damage (H318).
• Precautionary Measures:
  • P280: Wear protective gloves/eye protection.
  • P305+P351+P338: Rinse eyes cautiously if exposed.
• Storage Conditions: Store at temperatures between 2–8°C in a tightly sealed container to avoid moisture absorption.

Regulatory Information

This compound is expected to comply with TSCA regulations but should be verified for specific handling requirements based on local regulations.

This compound is commercially available in various quantities for research purposes and is integral to organic synthesis and biochemical applications.

Citations:

1. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8972547.htm
2. https://www.lookchem.com/ProductWholeProperty_LCPL304680.htm
3. https://www.sigmaaldrich.com/US/en/product/aldrich/772321
4. https://cymitquimica.com/products/TR-T224950/43225-70-3/mixture-of-1235-tetra-o-acetyl-d-arabinofuranose-and-1234-tetra-o-acetyl-d-arabinopyranose-mixture/
5. https://pubchem.ncbi.nlm.nih.gov/compound/1_2_3_5-Tetra-O-acetyl-a-D-arabinofuranose
6. https://cymitquimica.com/cas/43225-70-3/?items=100
7. https://www.pharmaffiliates.com/en/79120-81-3-1-2-3-5-tetra-o-acetyl-alpha-l-arabinofuranose-pa280201004.html
8. https://www.simsonpharma.com/product/1,2,3,5-tetra-o-acetyl-alpha-d-arabinofuranose
9. https://www.amadischem.com/product-A1251150
10. https://www.lgcstandards.com/CN/en/Mixture-of-1-2-3-5-Tetra-O-acetyl-D-arabinofuranose-and-1-2-3-4-Tetra-O-acetyl-D-arabinopyranose-Alpha-Beta-mixture-/p/TRC-T224950