1056899-49-0

Upstream product

• 695-96-5 2-bromo-4-chlorophenol 
• 121-97-1 4-Methoxypropiophenone 

Downstream Products

• 40341-58-0 (E)-2-(4-methoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan 
• 1609690-76-7 C₁₇H₁₃ClO₃ 
• 1609690-78-9 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl-β-D-glucopyranoside 
• 1609690-79-0 4-[5-chloro-3-methylbenzofuran-2-yl]phenyltetra-O-acetyl-β-L-glucopyranoside 
• 1609690-80-3 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl tetra-O-acetyl-β-D-galactopyranoside 
• 1609690-81-4 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl tetra-O-acetyl-β-L-galactopyranoside 
• 1609690-82-5 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl tri-O-acetyl-β-L-fucopyranoside 
• 1609690-83-6 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl-β-L-glucopyranoside 
• 1609690-84-7 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl-β-D-galactopyranoside 
• 1609690-85-8 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl-β-L-galactopyranoside 
• 1609690-87-0 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl tetra-O-benzoyl-α-D-mannopyranoside 
• 1609690-90-5 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl tri-O-benzoyl-α-L-rhamnopyranoside 
• 1609690-91-6 4-[5-chloro-3-methylbenzofuran-2-yl]phenyl-α-L-rhamnopyranoside 
• 1609690-73-4 5-chloro-2-(4-hydroxyphenyl)-3-methylbenzofuran 

Relevant academic research and scientific papers

Di-tert-butylneopentylphosphine (DTBNpP): An Efficient Ligand in the Palladium-Catalyzed α-Arylation of Ketones

Di-tert-butylneopentylphosphine (DTBNpP) and palladium(II) acetate provide an efficient catalytic system for the α-arylation of ketones. Aryl bromides were coupled with ketones using 0.25-0.5 mol-% Pd(OAc)2/DTBNpP in toluene at 50 C, whereas aryl chlorides required a higher catalyst loading (0.5-2.0 mol-%) and a higher temperature (80 C). Coupling of 2-bromophenol with ketones using the Pd/DTBNpP system provides an efficient route for the synthesis of benzofurans.

Synthesis of potential allosteric modulators of Hsp90 by chemical glycosylation of Eupomatenoid-6

Hsp90 (Heat shock protein-90) is a chaperone protein and an established anti-apoptotic target in cancer therapy. Most of the known small-molecule inhibitors that have shown potent antitumor activity target the Hsp90 N-terminal domain and directly inhibit its ATP-ase activity. Many of these molecules display important secondary effects. A different approach to Hsp90 inhibition consists of targeting the protein C-terminal domain (CTD) and modulating its chaperone activity through allosteric effects. Using an original computational approach, allosteric hot-spots in the CTD have been recently identified that control interdomain communication. A combination of virtual and experimental screening enabled identification of a rhamnosylated benzofuran (Eupomatenoid-2) as a lead for further development. In this paper we describe glycodiversification of Eupomatenoid-2 using chemical glycosylation of the 2-(4′-hydroxyphenyl)benzofuran aglycon (a.k.a. Eupomatenoid-6). Glycosylation of the phenol by glycosyl bromides under basic conditions afforded the desired products in the gluco-, galacto-, and fuco-series. This approach failed in the manno- and rhamno-series. However, mannosylation and rhamnosylation of Eupomatenoid-6 could be obtained under carefully controlled acidic conditions, using O-benzoxazolyl imidate (OBox) donors. The glycosides obtained are currently under investigation as modulators of Hsp90 chaperone activity.

One-pot synthesis of benzofurans via palladium-catalyzed enolate arylation with o-bromophenols

(Chemical Equation Presented) A one-pot synthesis of benzofurans which utilizes a palladium-catalyzed enolate arylation is described. The process demonstrates broad substrate scope and provides differentially substituted benzofurans in moderate to excelle