7696-34-6

Upstream product

• 101231-54-3 O²,O³,O⁴-triacetyl-O¹-(2-methoxycarbonyl-phenyl)-β-D-glucopyranuronic acid methyl ester 
• 138-52-3 D-(-)-salicin 
• 119-36-8 methyl salicylate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 

Relevant academic research and scientific papers

Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO

The carbohydrates 4-15 are anodically oxidized with 2,2,6,6- tetramethylpiperidin-1-oxyl (TEMPO) as mediator. Selective and complete reaction at the primary hydroxyl groups affords the corresponding carboxylic acids 16-32 in moderate to excellent yield. Methyl α-D-glucopyranoside is converted in 98% yield to the uronic acid 16. Cyclic voltammetry shows that the oxydation is base-catalyzed and the oxidation of the hydroxy group with TEMPO+ (2) is rate determining.