1,2,3,4-Tetra-O-pivaloyl-β-D-glucuronic Acid Methyl Ester

1,2,3,4-Tetra-O-pivaloyl-β-D-glucuronic Acid Methyl Ester

1,2,3,4-Tetra-O-pivaloyl-β-D-glucuronic acid methyl ester is a chemically modified glucuronic acid derivative that serves as an important intermediate in carbohydrate chemistry and organic synthesis. This compound is characterized by its protective pivaloyl groups and methyl ester functionality, which enhance its reactivity and stability for various applications.

Chemical Identity

• CAS Number: 248939-38-0
• Product Code: A1251262
• IUPAC Name: (2S,3R,4S,5S)-3,4,5-tris(2,2-dimethylpropanoate)oxane-2-carboxylic acid methyl ester
• Molecular Formula: C₂₇H₄₄O₁₁
• Molecular Weight: 544.63 g/mol

Physical Properties

• Appearance: White to off-white crystalline solid
• Purity: ≥97% (commonly verified via NMR spectroscopy)
• Melting Point: Not explicitly listed but typically stable under standard laboratory conditions.
• Solubility: Soluble in polar organic solvents such as dichloromethane and methanol; insoluble in water.
• Storage Conditions: Store at 2–8°C for long-term stability.

Structural Features

This compound features:

• A β-D-glucuronic acid backbone with four pivaloyl groups attached at the 1, 2, 3, and 4 positions.
• A methyl ester at the carboxylic acid group (C6), which enhances its stability and facilitates further chemical reactions.
• The pivaloyl groups serve to protect the hydroxyl functionalities during chemical reactions.

Applications

1,2,3,4-Tetra-O-pivaloyl-β-D-glucuronic acid methyl ester is utilized in various fields:

• Glycosylation Reactions: Acts as a glycosyl donor for synthesizing complex carbohydrates and glycoconjugates.
• Organic Synthesis: Used in the preparation of glycosides and other carbohydrate derivatives.
• Pharmaceutical Research: Plays a role in developing carbohydrate-based drugs and enzyme inhibitors due to its ability to modulate biological activity.
• Biochemical Studies: Employed in research involving carbohydrate-protein interactions and enzymatic mechanisms.

Safety and Handling

• Hazard Statements: Generally considered safe when handled properly; however, standard laboratory precautions should be observed.
• Storage Conditions: Store at 2–8°C in a tightly sealed container to prevent 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.

1,2,3,4-Tetra-O-pivaloyl-β-D-glucuronic acid methyl ester is commercially available for research purposes and is integral to advancing carbohydrate chemistry and related fields. Its unique structure allows for versatile applications in both synthetic and analytical chemistry.

Citations:

1. https://goldbio.com/product/4025/1234-tetra-o-acetyl-b-d-glucuronic-acid-methyl-ester
2. https://ie.vwr.com/store/product/34584357/methyl-1-2-3-4-tetra-o-pivaloyl-b-d-glucopyranosyluronate-98
3. https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-1_2_3_4-tetra-O-acetyl-D-glucopyranuronate
4. https://uk.vwr.com/store/product/34584357/methyl-1-2-3-4-tetra-o-pivaloyl-b-d-glucopyranosyluronate-98
5. https://synthose.com/products/MG207
6. https://synthose.com/products/MG293
7. https://www.glentham.com/en/products/product/GC7693/
8. https://www.bocsci.com/product/1-2-3-4-tetra-o-pivaloyl-b-d-glucuronide-methyl-cas-86448-91-1-119.html