1,2,3,4-tetra-O-acetyl-β-D-pyranouronic acid methyl ester, CAS No. 7355-18-2

Welcome to iChemical.com!

In the below part, please select the country you want us to ship to: Please note that once you've selected a shipping country, all pricing information on our website will be automatically updated to include door-to-door shipping to the country you specified.

North America

South America

Africa

Europe

Asia

Oceania

7355-18-2

Catalog No. EBD2204848

CAS 7355-18-2

Name 1,2,3,4-tetra-O-acetyl-β-D-pyranouronic acid methyl ester

Get Quote

Basic Information

Synonyms: methyl1,2,3,4-tetra-O-acetyl-β-D-glucopyranosiduronate 1,2,3,4-tetra-O-acetyl-β-D-pyranouronicacidmethylester methyl1,2,3,4-tetra-O-acetyl-B-D-*glucuronate MethylO-tetraacetyl-beta-D-glucopyranuronate beta-D-Glucopyranuronicacid,methylester,tetraacetate methyl1,2,3,4-tetra-O-acetyl-beta-D-glucopyranuronate methyl1,2,3,4-tetra-O-acetylhexopyranuronate Methyl1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate (2S,3S,4S,5R,6S)-methyl3,4,5,6-tetraacetoxy-tetrahydro-2H-pyran-2-carboxylate

Molecular Formula: C15H20O11

Molecular Weight: 376.31

MDL Number: MFCD00069834

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

1,2,3,4-Tetra-O-acetyl-D-glucuronic acid methyl ester is a fully acetylated derivative of D-glucuronic acid methyl ester. It is a white to off-white crystalline powder with a molecular formula of C15H20O12 and a molecular weight of 392.31 g/mol. This compound is a key protected intermediate in carbohydrate chemistry, featuring acetyl groups protecting the hydroxyl functionalities and a methyl ester protecting the carboxylic acid group. Its primary application is in the synthesis of more complex glycosides, glycoconjugates, and oligosaccharides. After selective deprotection steps, it serves as a crucial building block for preparing glucuronides, which are important metabolites of many drugs and xenobiotics. It is widely used in medicinal chemistry and biochemical research for the synthesis of substrates for glucuronosyltransferase enzymes and for producing standards in drug metabolism studies. As a protected sugar derivative, it is a valuable chiral synthon in organic synthesis. The acetyl groups facilitate purification and enhance the stability of the molecule during synthetic manipulations. It is a common starting material for generating glycosyl donors (e.g., glycosyl bromides or trichloroacetimidates) used in glycosylation reactions to construct biologically active molecules.

Physical Properties

Melting Point: 179 °C

Boiling Point: 412.3 °C at 760 mmHg

Flash Point: 178.4 °C

Density: 1.33 g/cm3

Refractivity: 8.0 ° (C=1, CHCl3)

Storage: 2-8°C