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