15548-42-2

Upstream product

• 37797-55-0 1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 108-95-2 phenol 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1259428-56-2 phenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 1093111-23-9 phenyl 2,3:4,6-di-O-isopropylidene-β-D-mannopyranoside 
• 100-67-4 potassium phenolate 
• 70835-78-8 2,3:4,6-di-O-cyclohexylidene-α-D-mannopyranose 
• 72200-60-3 β- 
• 83-87-4 D-Mannose pentaacetate 

Downstream Products

• 119125-08-5 phenyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside 
• 119125-14-3 methyl 2,3-dideoxy-2-C-p-tolylsulfonyl-α-D-erythro-hexopyranosid-4-ulose 
• 119125-06-3 1,5-anhydro-4,6-O-benzylidene-2-deoxy-3-O-methyl-2-C-p-tolylsulfonyl-D-ribo-hex-1-enitol 
• 119125-11-0 methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-α-D-erythro-hex-3-enopyranoside 
• 119125-15-4 methyl 4,6-di-O-acetyl-2,3-dideoxy-2-C-p-tolylsulfonyl-α-D-xylo-hexopyranosie 
• 119125-16-5 phenyl 4,6-O-benzylidene-2-deoxy-3-O-methyl-2-C-p-tolylsulfonyl-α-D-glucopyranosie 
• 119125-10-9 methyl 4,6-O-benzylidene-2-deoxy-3-O-methyl-2-C-p-tolylsulfonyl-α-D-altropyranoside 
• 119125-12-1 methyl 4,6-O-benzylidene-2-deoxy-3-O-methyl-2-C-p-tolylsulfonyl-α-D-allopyranoside 
• 119125-05-2 phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-α-D-erythro-hex-2-enopyranoside 
• 119125-09-6 phenyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-2-C-p-tolylsulfonyl-α-D-mannopyranoside 
• 849938-02-9 phenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 357187-42-9 phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 878806-04-3 phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2-O-benzyl-4,6-benzylidene-α-D-mannopyranoside 
• 878806-19-0 phenyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Phenyl glycosides – Solid-state NMR, X-ray diffraction and conformational analysis using genetic algorithm

The X-ray structures of 2,6-dimethylphenyl and phenyl 2,3,4,6-tetra-O-acetyl β-glucosides (1 and 3) and phenyl α-mannoside (6) were obtained. The independent part of the unit cell of the glycosides 1 and 6 was formed by one molecule, and for the glucoside 3, two molecules in the crystal cell were observed. In deacetylated glycosides 4 and 6 the crystal structure was established by a hydrogen bond network formed between the sugar hydroxyls and solvent molecules. The 13C CPMAS NMR spectra of aryl glycosides 1–6 were analysed. In the spectrum of 3, doubling of the C4 aryl signal was observed which confirmed the presence of two independent molecules in the solid sample. The GAAGS (Genetic Algorithm-Assisted Grid Search) method was used to determine the low-energy conformers of α-mannosides and β-glucosides. The orientation of the aryl pendant group was calculated using Molecular Mechanics (MMFF94) as well as Quantum Mechanics theory (DFT, B3LYP/6-31 + G(d,p)).

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

The present invention encompasses compounds and methods for treating urinary tract infections.

FimH antagonists for the oral treatment of urinary tract infections: From design and synthesis to in vitro and in vivo evaluation

Urinary tract infection (UTI) by uropathogenic Escherichia coli (UPEC) is one of the most common infections, particularly affecting women. The interaction of FimH, a lectin located at the tip of bacterial pili, with high mannose structures is critical for the ability of UPEC to colonize and invade the bladder epithelium. We describe the synthesis and the in vitro/in vivo evaluation of α-d-mannosides with the ability to block the bacteria/host cell interaction. According to the pharmacokinetic properties, a prodrug approach for their evaluation in the UTI mouse model was explored. As a result, an orally available, low molecular weight FimH antagonist was identified with the potential to reduce the colony forming units (CFU) in the urine by 2 orders of magnitude and in the bladder by 4 orders of magnitude. With FimH antagonist 16b, the great potential for the effective treatment of urinary tract infections with a new class of orally available antiinfectives could be demonstrated.

Conformational choice and selectivity in singly and multiply hydrated monosaccharides in the gas phase

Factors governing hydration, regioselectivity and conformational choice in hydrated carbohydrates have been examined by determining and reviewing the structures of a systematically varied set of singly and multiply hydrated monosaccharide complexes in the gas phase. This has been achieved through a combination of experiments, including infrared ion-depletion spectroscopy conducted in a supersonic jet expansion, and computation through molecular mechanics, density functional theory (DFT) and ab initio calculations. New spectroscopic and/or computational results obtained for the singly hydrated complexes of phenyl β-D-mannopyranoside (β-D-PhMan), methyl α-D-gluco- and α-D-galactopyranoside (α-D-MeGlc and α-D-MeGal), when coupled with those reported earlier for the singly hydrated complexes of α-D-PhMan, β-D-PhGlc and β-D-PhGal, have created a comprehensive data set, which reveals a systematic pattern of conformational preference and binding site selectivity, driven by the provision of optimal, co-operative hydrogen-bonded networks in the hydrated sugars. Their control of conformational choice and structure has been further revealed through spectroscopic and/or computational investigations of a series of multiply hydrated complexes: they include β-D-PhMan-(H2O)2,3- which has an exocyclic hydroxymethyl group, and the doubly hydrated complex of phenyl α-L-fucopyranoside, α-L-PhFuc-(H2O)2, which does not. Despite the very large number of potential structurediggers and binding sites, the choice is highly selective with binding invariably focussed around the hydroxymethyl group (when present). In β-D-PhMan-(H2O)2,3, the bound water molecules are located exclusively on its polar face and their orientation is dictated by the (perturbed) conformation of the carbohydrate to which they are attached. The possible operation of similar rules governing the structures of hydrogen-bonded protein-carbohydrate complexes is proposed.

Stannic chloride promoted synthesis of mannosides

Use of anhyd.SnCl4 has been described for the synthesis of aryl, arylalkyl and alkyl α-D-mannopyranosides.A possible mechanism for the formation of α-anomer in these reactions is discussed.

Rates of Acidic and Alkaline Hydrolysis of Substituted Phenyl α- and βDMannopyranosides

The rates of hydrolysis of substituted phenyl α- and β-D-mannopyranosides were measured in acidic and alkaline solutions.In 0.11 N hydrochloric acid solution, the α-mannosides were hydrolyzed faster than the corresponding β-anomers.The rates of hydrolysis for the α-mannosides were unaffected by substitution in the phenyl group (Hammett reaction constant ρ=-0.07+/-0.065 (S.D.)), and those for the β-mannosides were slightly enhanced by the introduction of electron-releasing substituents (ρ=-0.25+/-0.082).In sodium hydroxide solution, the α-mannosides liberated their aglycones, phenols, much faster than the corresponding β-anomers and the rates were enhanced by the introduction of electron-withdrawing substituents (ρ=+2.7+/-0.14 for the α-, +3.1+/-0.46 for the β-mannosides, each in 3.93 N NaOH).Phenyl α-mannoside was hydrolyzed much faster than phenyl β-glucoside, though both have trans-1,2 configuration, indicating the importance of a 1,2-diaxial orientation for the reaction. Keywords --- aryl α-mannopyranoside; aryl β-mannopyranoside; acid hydrolysis; alkaline hydrolysis; Hammett plot