131433-03-9

Basic information

• Product Name: methyl 4,6-O-benzylidene-β-D-galactopyranoside
• Synonyms: methyl 4,6-O-benzylidene-β-D-galactopyranoside
• CAS NO: 131433-03-9
• Molecular Weight: 282.293
• Mol File: 131433-03-9.mol
• Article Data: 47

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-benzylidene-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-β-D-galactopyranoside(131433-03-9)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-β-D-galactopyranoside(131433-03-9)

Safety Data

• Hazardous Substances Data: 131433-03-9(Hazardous Substances Data)

Upstream product

• 51223-62-2 methyl β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 100-52-7 benzaldehyde 
• 2774-22-3 2,3-O-diacetyl-(4,6-O-benzylidene)methyl-α-D-mannopyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 22277-65-2 Methyl mannoside 
• 82430-07-7 (4S,5R)-5-((R)-1-Methoxy-2-oxo-ethoxy)-2-phenyl-[1,3]dioxane-4-carbaldehyde 
• 82430-07-7 (2R,4S,5R)-5-((R)-1-Methoxy-2-oxo-ethoxy)-2-phenyl-[1,3]dioxane-4-carbaldehyde 
• 3396-99-4 methyl α-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 774-48-1 (diethoxymethyl)benzene 
• 1769-06-8 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-mannopyranoside 

Downstream Products

• 74984-87-5 Methyl-4,5-O-benzyliden-2,3-carbonato-α-D-mannopyranosid 
• 120200-50-2 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-mannopyranoside 
• 93237-53-7 methyl 4,6-O-benzylidene-2,3-di-O-(N-imidazoylsulfonyl)-β-D-galactopyranoside 
• 7115-19-7 methyl β-D-galactopyranosyl-<1->3>-β-D-galactopyranoside 
• 18449-79-1 Methyl O-α-D-galactopyranosyl-(1->3)-β-D-galactopyranoside 
• 78120-15-7 methyl β-D-galactopyranosyl-<1->2>-β-D-galactopyranoside 
• 81086-87-5 methyl 2-O-α-D-galactopyranosyl-β-D-galactopyranoside 
• 15384-57-3 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside 
• 124662-96-0 Methyl 4,6-O-benzylidene-β-D-galactopyranoside 3-(phenylsulfate) 
• 124662-93-7 Methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-(phenylsulfate) 
• 82430-07-7 (2R,4S,5R)-5-((R)-1-Methoxy-2-oxo-ethoxy)-2-phenyl-[1,3]dioxane-4-carbaldehyde 
• 2880-96-8 (1aR,2S,6R,7aR,7bR)-2-Methoxy-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 2880-96-8 (1aS,2S,6R,7aR,7bS)-2-Methoxy-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 151526-84-0 methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-bis(methanesulfonate) 

Relevant articles and documents

Synthesis of benzylidenated hexopyranosides in ionic liquids

The synthesis of 4,6-O-benzylidenated monosaccharides and disaccharides has been studied using ionic liquids as a unique solvent alternative. An examination of several imidazolium ionic liquids indicates that the benzylidenation of hexopyranosides in 3-bu

Exploration of the Fluoride Reactivity of Aryltrifluoroborate on Selective Cleavage of Diphenylmethylsilyl Groups

The first known report on the fluoride catalytic reactivity of potassium aryltrifluoroborate is described. The fluoride reactivity of phenyltrifluoroborate was controlled by substituents on the trifluoroborate-attached benzene, such as the methoxy group a

Binding of the Bacterial Adhesin FimH to Its Natural, Multivalent High-Mannose Type Glycan Targets

Multivalent carbohydrate-lectin interactions at host-pathogen interfaces play a crucial role in the establishment of infections. Although competitive antagonists that prevent pathogen adhesion are promising antimicrobial drugs, the molecular mechanisms underlying these complex adhesion processes are still poorly understood. Here, we characterize the interactions between the fimbrial adhesin FimH from uropathogenic Escherichia coli strains and its natural high-mannose type N-glycan binding epitopes on uroepithelial glycoproteins. Crystal structures and a detailed kinetic characterization of ligand-binding and dissociation revealed that the binding pocket of FimH evolved such that it recognizes the terminal α(1-2)-, α(1-3)-, and α(1-6)-linked mannosides of natural high-mannose type N-glycans with similar affinity. We demonstrate that the 2000-fold higher affinity of the domain-separated state of FimH compared to its domain-associated state is ligand-independent and consistent with a thermodynamic cycle in which ligand-binding shifts the association equilibrium between the FimH lectin and the FimH pilin domain. Moreover, we show that a single N-glycan can bind up to three molecules of FimH, albeit with negative cooperativity, so that a molar excess of accessible N-glycans over FimH on the cell surface favors monovalent FimH binding. Our data provide pivotal insights into the adhesion properties of uropathogenic Escherichia coli strains to their target receptors and a solid basis for the development of effective FimH antagonists.