287967-74-2

Basic information

• Product Name: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• Synonyms: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 287967-74-2
• Molecular Weight: 550.301
• Mol File: 287967-74-2.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(287967-74-2)
• EPA Substance Registry System: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(287967-74-2)

Safety Data

• Hazardous Substances Data: 287967-74-2(Hazardous Substances Data)

Upstream product

• 83-87-4 D-Mannose pentaacetate 
• 540-38-5 p-Iodophenol 
• 121238-27-5 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 22860-22-6 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose 
• 530-26-7 D-Mannose 

Downstream Products

• 287967-77-5 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[3-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenoxy}-tetrahydro-pyran-3-yl ester 
• 1295649-89-6 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1312313-03-3 4'-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)biphenyl-4-yl-(morpholino)methanone 
• 1312312-41-6 4-(5-nitroindolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1312312-95-0 methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate 
• 1312312-42-7 4-(5-nitroindolin-1-yl)phenyl α-D-mannopyranoside 
• 677352-87-3 4-ethynylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1318797-50-0 4,4'-bis-(α-D-mannopyranosyloxy)biphenyl 
• 1318797-55-5 bis[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne 
• 871311-10-3 bis[4-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne 
• 694520-16-6 C₂₅H₃₂O₁₀Si 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1312312-43-8 4-(indolin-1-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1312313-12-4 4'-(α-D-mannopyranosyloxy)-N-methylbiphenyl-4-sulfonamide 

Relevant articles and documents

Preparation and characterization of glycopolymers with biphenyl spacers: Via Suzuki coupling reaction

Poly(vinylbiphenyl)s bearing glycoside ligands at the side chains were prepared using the Suzuku coupling reaction. Effects of glycoside reactant concentration, halide species, glycoside species, and catalyst species on the incorporation of glycoside ligand into the polymer were investigated. The obtained glycopolymers exhibited specific binding to proteins corresponding to the glycoside ligands. In addition, the biphenyl spacers formed by the Suzuki coupling reaction in the glycopolymer were fluorescent, whereas the polymer precursor was not.

Antiadhesion therapy for urinary tract infections-A balanced PK/PD profile proved to be key for success

The initial step for the successful establishment of urinary tract infections (UTIs), predominantly caused by uropathogenic Escherichia coli, is the adhesion of bacteria to urothelial cells. This attachment is mediated by FimH, a mannose-binding adhesin, which is expressed on the bacterial surface. To date, UTIs are mainly treated with antibiotics, leading to the ubiquitous problem of increasing resistance against most of the currently available antimicrobials. Therefore, new treatment strategies are urgently needed, avoiding selection pressure and thereby implying a reduced risk of resistance. Here, we present a new class of highly active antimicrobials, targeting the virulence factor FimH. When the most potent representative, an indolinylphenyl mannoside, was administered in a mouse model at the low dosage of 1 mg/kg (corresponding to approximately 25 μg/mouse), the minimal therapeutic concentration to prevent UTI was maintained for more than 8 h. In a treatment study, the colony-forming units in the bladder could be reduced by almost 4 orders of magnitude, comparable to the standard antibiotic treatment with ciprofloxacin (8 mg/kg, sc).

Synthesis of a small library of bivalent α-d-mannopyranosides for lectin cross-linking

A small library of bivalent α-d-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl α-d-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling.

MANNOSE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION

Compounds of the formula (I) wherein n is 0, 1 or 2, R1 is aryl, heteroaryl or heterocyclyl, and R2 and R3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli.

Synthesis of "sugar-rods" with phytohemagglutinin cross-linking properties by using the palladium-catalyzed Sonogashira reaction

A palladium-catalyzed Sonogashira reaction has been applied for the syntheses of divalent "sugar-rods" which exhibited excellent lectin cross-linking properties. The procedure, which involves a tetrakis(triphenylphosphine)-palladium-catalyzed cross-coupling reaction between an alkyne and a halogenbearing sp2-carbon in DMF at 60°C, is very efficient and the dimeric or heterobifunctional "sugar-rods" (8-13, 15-17) were isolated in 65-100% yields. Dimers 8 a and 15a were both shown to form insoluble cross-linked lattices when mixed with the tetrameric plant lectin from Canavalia ensiformis (Concavalin A, Con A). Moreover, the relative inhibitory properties of the synthetic dimannosides were determined by means of the hemagglutination of rabbit erythrocytes, whereby dimer 15a was shown to be 20-fold more potent than monomeric methyl α-D-mannopyranoside.