10357-03-6

Basic information

• Product Name: methyl (methyl α,β-D-galactopyranosid)uronate
• CAS NO: 10357-03-6
• Molecular Weight: 222.195
• Mol File: 10357-03-6.mol
• Article Data: 5

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(10357-03-6)
• EPA Substance Registry System: methyl (methyl α,β-D-galactopyranosid)uronate(10357-03-6)

Safety Data

• Hazardous Substances Data: 10357-03-6(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 685-73-4 D-galacturonic acid 
• 5241-02-1 O¹-methyl-β-D-galactopyranuronic acid 
• 643-33-4 D-galacturonic acid 
• 4356-82-5 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 62435-44-3 methyl (methyl 2,3,4-tri-O-benzyl-β-D-galactopyranosid)uronate 
• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 18311-26-7 methyl 6-O-triphenylmethyl-β-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 124-41-4 sodium methylate 
• 73977-52-3 2,4-di-O-acetyl-β-methyl-D-galactopyranosideuronic acid γ-lactone 
• 616-42-2 dimethylsulfite 

Relevant articles and documents

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

SYNTHESIS OF METHYL ETHERS OF METHYL (METHYL β-D-GALACTOPYRANOSID) URONATE

The oxidation of methyl β-D-galactopyranoside with oxygen in the presence of platinum and carbon gave methyl (methyl β-D-galactopyranosid)uronate, (I) with a yield of 20percent.The partial methylation of (I) with methyl iodide in the presence of silver ox

PROTON AND CARBON-13 NUCLEAR MAGNETIC RESONANCE STUDIES ON METHYL (METHYL D-GALACTOSID)URONATES AND THEIR PER-O-ACETYL DERIVATIVES

The 1H- and 13C-n.m.r. spectra of the anomeric methyl (methyl D-galactosid)uronates, as well as the 1H-n.m.r. spectra of their acetyl derivatives, were analyzed.The spectra of the unacetylated D-galactopyranosiduronates showed good correlation with those of the corresponding anomeric D-galactopyranuronic acids and their methyl esters, and with those of the anomeric methyl D-galactopyranosides.From the values of the chemical shifts and coupling constants, it was concluded that the anomeric methyl (methyl D-galactopyranosid)uronates and their corrasponding peracetates are in the 4C1(D) conformation.The chemical shifts in the 13C-n.m.r. spectra show good correlation with those of the methyl D-galactosides.The signals of the furanose derivatives appear at fields lower than those of the corresponding pyranose compounds.