114297-26-6

Basic information

• Product Name: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose
• Synonyms: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose
• CAS NO: 114297-26-6
• Molecular Weight: 465.457
• Mol File: 114297-26-6.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose(114297-26-6)
• EPA Substance Registry System: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose(114297-26-6)

Safety Data

• Hazardous Substances Data: 114297-26-6(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 14131-63-6 D-glucosamine hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 51471-40-0 2--2-deoxy-D-glucopyranose 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 14131-62-5 D-glucosamine hydrochloride 

Downstream Products

• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 17460-45-6 tetra-acetyl glucosamine 
• 5432-46-2 acetyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranoside hydrochloride 
• 5348-99-2 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside 
• 99194-76-0 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranose 
• 1274877-74-5 3,4,6,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranosyl-(2-1)-3,4,6-tri-O-acetyl-2-deoxy-2-benzylcarbamate-β-D-glucopyranoside 
• 1274877-71-2 3,4,6,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranosyl-(2-1)-3,4,6-tri-O-acetyl-2-deoxy-2-benzylcarbamate-α-D-glucopyranoside 
• 1313741-19-3 C₄₉H₅₅NO₁₂ 
• 1203584-55-7 tert-butyldiphenylsilyl 3,4,6-tri-O-benzyl-2-deoxy-2-(4-methoxybenzylideneamino)-β-D-glucopyranose 
• 1203584-64-8 tert-butyldiphenylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranose 
• 1203584-66-0 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranosyl N-(phenyl)trifluoroacetimidate 
• 1203584-65-9 tert-butyldiphenylsilyl 3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranose 
• 1203584-67-1 3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-D-glucopyranosyl N-(phenyl)trifluoroacetimidate 
• 1203584-56-8 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranoside 

Relevant articles and documents

Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

Method for preparing 2-deoxy-D-glucose

The invention discloses a method for preparing 2-deoxy-D-glucose. According to the method, D-glucosamine which is low in price and easy to obtain serves as a starting material, p-anisaldehyde is used for protecting amino, pyridine serves as a solvent unde

Synthesis of antimicrobial glucosamides as bacterial quorum sensing mechanism inhibitors

Bacteria communicate with one another and regulate their pathogenicity through a phenomenon known as quorum sensing (QS). When the bacterial colony reaches a threshold density, the QS system induces the production of virulence factors and the formation of biofilms, a powerful defence system against the host's immune responses. The glucosamine monomer has been shown to disrupt the bacterial QS system by inhibiting autoinducer (AI) signalling molecules such as the acyl-homoserine lactones (AHLs). In this study, the synthesis of acetoxy-glucosamides 8, hydroxy-glucosamides 9 and 3-oxo-glucosamides 12 was performed via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N,N′-dicyclohexylcarbodiimide (DCC) coupling methods. All of the synthesized compounds were tested against two bacterial strains, P. aeruginosa MH602 (LasI/R-type QS) and E. coli MT102 (LuxI/R-type QS), for QS inhibitory activity. The most active compound 9b showed 79.1% QS inhibition against P. aeruginosa MH602 and 98.4% against E. coli MT102, while compound 12b showed 64.5% inhibition against P. aeruginosa MH602 and 88.1% against E. coli MT102 strain at 2?mM concentration. The ability of the compounds to inhibit the production of the virulence factor pyocyanin and biofilm formation in the P. aeruginosa (PA14) strain was also examined. Finally, computational docking studies were performed with the LasR receptor protein.