19887-82-2

Upstream product

• 5346-66-7 2-methylphenyl-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside 
• 95-48-7 ortho-cresol 
• 122186-40-7 2-(2,3,4,6-tetra-O-acetyl-β-_D-glucopyranozyloxy)benzyl alcohol 
• 60523-66-2 2-(2,3,4,6-tetra-О-acetyl-β-d-glucopyranosyloxy)benzyl bromide 
• 32742-28-2 2-methylphenyl-tetra-O-acetyl-α-D-glucopyranoside 
• 69-79-4 D-maltose 
• 84380-03-0 2-methylphenyl 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranoside 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 4163-60-4 β-D-galactose peracetate 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 138-52-3 D-(-)-salicin 

Downstream Products

• 115431-89-5 (2R,3R,4S,5R,6S)-3,4,5-Trimethoxy-2-methoxymethyl-6-o-tolyloxy-tetrahydro-pyran 
• 1400800-17-0 2-methylphenyl 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranoside 
• 115431-91-9 (2R,3R,4S,5R,6S)-3,4,5-Trimethoxy-2-methoxymethyl-6-(2-methyl-cyclohexa-1,4-dienyloxy)-tetrahydro-pyran 

Relevant academic research and scientific papers

Selective demethylation ofO-aryl glycosides by iridium-catalyzed hydrosilylation

The cleavage of alkyl ethers by hydrosilylation is a powerful synthetic tool for the generation of silyl ethers. Previous attempts to apply this transformation to carbohydrate derivatives have been constrained by poor selectivity and preferential reductio

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

The present invention is directed to various compounds, compositions, and methods for treating bacterial infections such as urinary tract infections.

Structure-based discovery of glycomimetic FmlH ligands as inhibitors of bacterial adhesion during urinary tract infection

Treatment of bacterial infections is becoming a serious clinical challenge due to the global dissemination of multidrug antibiotic resistance, necessitating the search for alternative treatments to disarm the virulence mechanisms underlying these infections. Uropathogenic Escherichia coli (UPEC) employs multiple chaperone- usher pathway pili tipped with adhesins with diverse receptor specificities to colonize various host tissues and habitats. For example, UPEC F9 pili specifically bind galactose or N-acetylgalactosamine epitopes on the kidney and inflamed bladder. Using X-ray structureguided methods, virtual screening, and multiplex ELISA arrays, we rationally designed aryl galactosides and N-acetylgalactosaminosides that inhibit the F9 pilus adhesin FmlH. The lead compound, 29β-NAc, is a biphenyl N-acetyl-β-galactosaminoside with a Ki of ～90 nM, representing a major advancement in potency relative to the characteristically weak nature of most carbohydrate-lectin interactions. 29β-NAc binds tightly to FmlH by engaging the residues Y46 through edge-to-face π-stacking with its A-phenyl ring, R142 in a salt-bridge interaction with its carboxylate group, and K132 through watermediated hydrogen bonding with its N-acetyl group. Administration of 29β-NAc in a mouse urinary tract infection (UTI) model significantly reduced bladder and kidney bacterial burdens, and coadministration of 29β-NAc and mannoside 4Z269, which targets the type 1 pilus adhesin FimH, resulted in greater elimination of bacteria from the urinary tract than either compound alone. Moreover, FmlH specifically binds healthy human kidney tissue in a 29β-NAc-inhibitable manner, suggesting a key role for F9 pili in human kidney colonization. Thus, these glycoside antagonists of FmlH represent a rational antivirulence strategy for UPEC-mediated UTI treatment.

A new look at acid catalyzed deacetylation of carbohydrates: A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides

In the present work we report that acetyl groups of per – acetylated aryl glycosides have different reactivity during the acidic deacetylation using HCl/EtOH in CHCl3, which leads to preferential deacetylation at O-3, O-4 and O-6. Thereby, the one-step preparation of 2-O-acetyl aryl glycosides with simple aglycon was accomplished for the first time. It was proved that the found reagent is to be general and unique for the preparation of series of 2-О-acetyl aryl glycosides. We have determined the influence of both carbohydrate moiety and the aglycon on the selectivity of deacetylation reaction by kinetic experiments. Using DFT/B3LYP/6-31G(d,p) and semi-empirical АМ1 methods we have found that the highest activation barrier is for 2-О-acetyl group. This completely explains the least reactivity of 2-О-acetyl group.

Synthesis and structure of tricarbonyl(η6-arene)chromium complexes of phenyl and benzyl D-glycopyranosides

A series of 15 glycoside-derived tricarbonyl(η6-arene) chromium complexes were prepared in 19-87% yield by heating fully acetylated or methylated aryl O-, S-, N- and C-glycosides of D-glucopyranose and D-mannopyranose with hexacarbonylchromium.

Purification, characterization, and gene identification of an α-glucosyl transfer enzyme, a novel type α-glucosidase from Xanthomonas campestris WU-9701

The α-glucosyl transfer enzyme (XgtA), a novel type α-glucosidase produced by Xanthomonas campestris WU-9701, was purified from the cell-free extract and characterized. The molecular weight of XgtA is estimated to be 57 kDa by SDS-PAGE and 60 kDa by gel filtration, indicating that XgtA is a monomeric enzyme. Kinetic properties of XgtA were determined for α-glucosyl transfer and maltose-hydrolyzing activities using maltose as the α-glucosyl donor, and if necessary, hydroquinone as the acceptor. The Vmax value for α-glucosyl transfer activity was 1.3 × 10-2 (mM/s); this value was 3.9-fold as much as that for maltose-hydrolyzing activity. XgtA neither produced maltooligosaccharides nor hydrolyzed sucrose. The gene encoding XgtA that contained a 1614-bp open reading frame was cloned, identified, and highly expressed in Escherichia coli JM109 as the host. Site-directed mutagenesis identified Asp201, Glu270, and Asp331 as the catalytic sites of XgtA, indicating that XgtA belongs to the glycoside hydrolase family 13.

CHELATION CONTROLLED REGIOSELECTIVE ALKYLATION AND 1,4 CHIRALITY TRANSFER IN OPTICALLY ACTIVE 1-ALKOXY-1,4-CYCLOHEXADIENES

Chelation controlled alkylation of optically active 1-alkoxy-1,4-cyclohexadienes leads to a mixture of 1,4-cyclohexadienes 4a-c and 1,3-cyclohexadienes 5a-c.The regio- and diastereoselectivities depend upon the nature of the chiral auxiliary and the react