18486-38-9

Basic information

• Product Name: methyl (methyl α,β-D-galactopyranosid)uronate
• CAS NO: 18486-38-9
• Molecular Weight: 222.195
• Mol File: 18486-38-9.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl (methyl α,β-D-galactopyranosid)uronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (methyl α,β-D-galactopyranosid)uronate(18486-38-9)
• EPA Substance Registry System: methyl (methyl α,β-D-galactopyranosid)uronate(18486-38-9)

Safety Data

• Hazardous Substances Data: 18486-38-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 96553-02-5 methyl (28-Hydroxy-23,28-dioxoolean-12-en-3β-yl β-D-Glucopyranoside)uronate 
• 6556-12-3 D-glucuronic acid 
• 709-50-2 methyl beta-D-glucopyranoside 
• 30902-96-6 methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 77-76-9 2,2-dimethoxy-propane 
• 4356-84-7 methyl β-D-glucopyranosiduronic acid 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 643-33-4 D-galacturonic acid 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 

Downstream Products

• 108866-91-7 uridine diphosphate <6-³H>glucose 
• 169557-85-1 methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 

Relevant articles and documents

The improved synthesis of β-D-Glucuronides using TEMPO and t-butyl hypochlorite

TEMPO/t-BuOCl is used to oxidise β-D-glucosides to β-D-glacuronides in high yield as a pivotal step in the preparation of labelled glucuronides from labelled glucose samples.

Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists

Carbohydrates are involved in many important pathological processes, such as bacterial and viral infections, by means of carbohydrate-protein interactions. Glycoconjugates with multiple carbohydrates are involved in multivalent interactions, thus increasing their binding strengths to proteins. In this work, we report the efficient synthesis of novel muramic and glucuronic acid glycodendrimers as potential Dengue virus antagonists. Aromatic scaffolds functionalized with a terminal ethynyl groups were coupled to muramic and glucuronic acid azides by click chemistry through optimized synthetic strategies to afford the desired glycodendrimers with high yields. Surface Plasmon Resonance studies have demonstrated that the compounds reported bind efficiently to the Dengue virus envelope protein. Molecular modelling studies were carried out to simulate and explain the binding observed. These studies confirm that efficient chemical synthesis of glycodendrimers can be brought about easily offering a versatile strategy to find new active compounds against Dengue virus.

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.