2,3,4-Tri-O-pivaloyl-β-D-glucopyranuronic acid methyl ester

2,3,4-Tri-O-pivaloyl-β-D-glucopyranuronic Acid Methyl Ester (CAS No. 86448-98-8)

2,3,4-Tri-O-pivaloyl-β-D-glucopyranuronic acid methyl ester is a chemically protected glucuronic acid derivative widely used in carbohydrate synthesis. Below is a comprehensive breakdown of its properties and applications:

Chemical Identity

• CAS Number: 86448-98-8
• Product Code: A1251263
• IUPAC Name: Methyl (2S,3S,4S,5R,6R)-3,4,5-tris(pivaloyloxy)-6-hydroxyoxane-2-carboxylate
• Molecular Formula: C₂₁H₃₂O₁₀
• Molecular Weight: 460.52 g/mol

Physical Properties

• Appearance: White crystalline solid
• Purity: ≥97% (typically confirmed via ¹H-NMR)
• Melting Point: 130–134°C
• Solubility: Soluble in DMSO, methanol, dichloromethane, and DMF.

Structural Features

• Based on the β-D-glucopyranuronic acid backbone with pivaloyl (trimethylacetyl) groups at the 2, 3, and 4 positions.
• A methyl ester at the carboxyl group (C6) stabilizes the uronic acid moiety.
• The β-anomeric configuration is retained, critical for stereospecific glycosylation reactions.

Applications

• Glycosylation Reactions: Serves as a key intermediate for synthesizing glycosides, glycoconjugates, or glycomimetics due to its stability and reactivity.
• Pharmaceutical Research: Used to develop prodrugs or enzyme substrates, leveraging its protected functional groups for targeted modifications.
• Biochemical Probes: Employed in studies involving carbohydrate-protein interactions.

Safety and Handling

• Hazard Statements: Not explicitly listed, but general precautions for organic esters apply:
  • Avoid inhalation, skin contact, and ingestion.
• Storage: Store at −20°C in a tightly sealed container to prevent moisture absorption.

Regulatory Information

• TSCA Status: Likely listed (similar glucuronic acid derivatives are TSCA-compliant).

This compound is commercially available in gram-scale quantities for research purposes, with applications in medicinal chemistry and glycobiology.

Citations:

1. https://pubchem.ncbi.nlm.nih.gov/compound/10782914
2. https://www.sigmaaldrich.com/IN/en/product/sigma/a8292
3. https://www.lookchem.com/CASDataBase_21085-72-3.htm
4. https://synthose.com/products/TG935
5. https://pubchem.ncbi.nlm.nih.gov/compound/171370124
6. https://synthose.com/products/TG137
7. https://www.amadischem.com/product-A1251262
8. https://www.ambeed.com/products/21085-72-3.html