31506-18-0

Basic information

• Product Name: Methyl 4-O-methyl-α-D-glucopyranosiduronic acid methyl ester
• Synonyms: Methyl 4-O-methyl-α-D-glucopyranosiduronic acid methyl ester
• CAS NO: 31506-18-0
• Molecular Formula: C9H16O7
• Molecular Weight: 236.21914
• Mol File: 31506-18-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 4-O-methyl-α-D-glucopyranosiduronic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-O-methyl-α-D-glucopyranosiduronic acid methyl ester(31506-18-0)
• EPA Substance Registry System: Methyl 4-O-methyl-α-D-glucopyranosiduronic acid methyl ester(31506-18-0)

Safety Data

• Hazardous Substances Data: 31506-18-0(Hazardous Substances Data)

Upstream product

• 51433-18-2 O²,O³-dibenzyl-O¹,O⁴-dimethyl-α-D-glucopyranuronic acid methyl ester 
• 186581-53-3 diazomethane 
• 51885-48-4 O¹,O⁴-dimethyl-α-D-glucopyranuronic acid amide 
• 18486-51-6 1-O-methyl-α-D-glucopyranuronic acid methyl ester 
• 74-88-4 methyl iodide 
• 73703-00-1 methyl 4-O-methyl-α-D-glucopyranosiduronic acid 
• 148312-82-7 methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 51885-48-4 O¹,O⁴-dimethyl-α-D-glucopyranuronic acid amide 

Relevant articles and documents

Synthesis and Rearrangement Reactions of Ester-Linked Lignin-Carbohydrate Model Compounds

A series of ester-linked lignin-carbohydrate model compounds has been synthesized, which represent possible ester linkages of lignin to hemicellulose in wood through the carboxylic acid group of 4-O-methyl-α-D-glucopyranosiduronic acid moieties.The threo and erythro isomers of these compounds were prepared through an appropriate combination of protective and stereoselective transformations.Spectroscopic characterization of these esters revealed that the uronosyl group migrated between the primary (γ) and benzylic (α) positions of the lignin side chain in both acidic and neutral conditions.It has been determined that the migration equilibrium favors γ- over α-esters, with the reaction possibly proceeding through a six-membered ring intermediate.That uronosyl migrations occur favoring the γ-position suggests that the classical view of lignin-xylan ester linkages in wood needs to be reevaluated.Keywords: Acyl migration; lignin-carbohydrate complexes; NMR