1415481-62-7

Basic information

• Product Name: biphenyl-4-yl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside
• Synonyms: biphenyl-4-yl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside
• CAS NO: 1415481-62-7
• Molecular Weight: 644.678
• Mol File: 1415481-62-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: biphenyl-4-yl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: biphenyl-4-yl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside(1415481-62-7)
• EPA Substance Registry System: biphenyl-4-yl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside(1415481-62-7)

Safety Data

• Hazardous Substances Data: 1415481-62-7(Hazardous Substances Data)

Upstream product

• 92-69-3 4-Phenylphenol 
• 83-87-4 D-Mannose pentaacetate 
• 1415481-61-6 biphenyl-4-yl 2,3,4-tri-O-benzoyl-6-O-trityl-α-D-mannopyranoside 
• 134698-98-9 p-phenylphenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 31909-79-2 (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(4-phenylphenoxy)-tetrahydropyran-3,4,5-triol 

Downstream Products

• 1415481-63-8 biphenyl-4-yl 2,3,4-tri-O-benzoyl-6-O-(methylthiomethyl)-α-D-mannopyranoside 
• 1415481-64-9 biphenyl-4-yl 2,3,4-tri-O-benzoyl-6-O-(phosphonooxy)methyl-α-D-mannopyranoside 

Relevant articles and documents

FimH Antagonists: Phosphate Prodrugs Improve Oral Bioavailability

The widespread occurrence of urinary tract infections has resulted in frequent antibiotic treatment, contributing to the emergence of antimicrobial resistance. Alternative approaches are therefore required. In the initial step of colonization, FimH, a lectin located at the tip of bacterial type 1 pili, interacts with mannosylated glycoproteins on the urothelial mucosa. This initial pathogen/host interaction is efficiently antagonized by biaryl α-d-mannopyranosides. However, their poor physicochemical properties, primarily resulting from low aqueous solubility, limit their suitability as oral treatment option. Herein, we report the syntheses and pharmacokinetic evaluation of phosphate prodrugs, which show an improved aqueous solubility of up to 140-fold. In a Caco-2 cell model, supersaturated solutions of the active principle were generated through hydrolysis of the phosphate esters by brush border-associated enzymes, leading to a high concentration gradient across the cell monolayer. As a result, the in vivo application of phosphate prodrugs led to a substantially increased Cmax and prolonged availability of FimH antagonists in urine.