20750-03-2

Basic information

• Product Name: methyl 3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside
• Synonyms: methyl 3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS NO: 20750-03-2
• Molecular Weight: 324.331
• Mol File: 20750-03-2.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: methyl 3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside(20750-03-2)
• EPA Substance Registry System: methyl 3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside(20750-03-2)

Safety Data

• Hazardous Substances Data: 20750-03-2(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 18031-56-6 methyl-[O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 2774-23-4 methyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 162226-16-6 Acetic acid (2R,4aR,6S,7R,8S,8aR)-7-allyloxycarbonyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 110-86-1 pyridine 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 1769-06-8 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 141-78-6 ethyl acetate 
• 1449790-66-2 methyl 3-O-acetyl-4,6-O-benzylidene-2-O-(N-phenylcarbamoyl)-α-D-mannopyranoside 
• 108-05-4 vinyl acetate 
• 14155-23-8 methyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 110715-29-2 methyl 4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside 
• 1449790-66-2 methyl 3-O-acetyl-4,6-O-benzylidene-2-O-(N-phenylcarbamoyl)-α-D-mannopyranoside 
• 51842-39-8 methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-methyl-α-D-glucopyranoside] 
• 440-06-2 methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-trifluoroacetyl-α-D-glucopyranoside] 
• 3053-12-1 methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 109454-71-9 methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-methanesulfonyl-α-D-glucopyranoside] 
• 98392-36-0 Methyl 2-O-acetyl-4,6-O-(phenylmethylene)-α-D-mannopyranoside 
• 2774-23-4 methyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1163704-46-8 methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1441884-65-6 C₃₆H₄₃BrO₁₄ 
• 1441884-73-6 C₃₆H₄₃BrO₁₄ 
• 1423010-15-4 (2R,4aR,5aS,8aS,9S,9aR)-5a-methoxy-7-oxo-2-phenyloctahydrofuro[2',3':5,6]pyrano[3,2-d][1,3]dioxin-9-yl acetate 
• 1353896-04-4 methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-acetyl-α-D-mannopyranoside 

Relevant articles and documents

Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts

Herein, we report the oligopeptide-catalyzed site-selective acylation of partially protected monosaccharides. We identified catalysts that invert site-selectivity compared to N-methylimidazole, which was used to determine the intrinsic reactivity, for 4,6

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.

Diisopropylethylamine-triggered, highly efficient, self-catalyzed regioselective acylation of carbohydrates and diols

A diisopropylethylamine (DIPEA)-triggered, self-catalyzed, regioselective acylation of carbohydrates and diols is presented. The hydroxyl groups can be acylated by the corresponding anhydride in MeCN in the presence of a catalytic amount of DIPEA. This method is comparatively green and mild as it uses less organic base compared with other selective acylation methods. Mechanistic studies indicate that DIPEA reacts with the anhydride to form a carboxylate ion, and then the carboxylate ion could catalyze the selective acylation through a dual H-bonding interaction.