163462-39-3

Upstream product

• 50638-08-9 5-bromo-3-methyl-1-benzofuran-2-carboxylic acid 
• 701262-40-0 5-bromo-2-(4-hydroxyphenyl)-3-methylbenzofuran 
• 568593-04-4 2-(4-Methoxy-phenyl)-3-methyl-5-((E)-propenyl)-benzofuran 

Downstream Products

• 1609690-96-1 E-[4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltri-O-benzoyl]-α-L-rhamnopyranoside 
• 1609690-97-2 Z-[4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltri-O-benzoyl]-α-L-rhamnopyranoside 
• 1609690-92-7 E-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-benzoyl-α-D-mannopyranoside 
• 1609690-93-8 Z-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-benzoyl-α-D-mannopyranoside 
• 1609691-02-2 E-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-L-glucopyranoside 
• 1609691-03-3 Z-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-L-glucopyranoside 
• 1609691-10-2 E-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-L-galactopyranoside 
• 1609691-11-3 Z-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-L-galactopyranoside 
• 1609693-91-5 E-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-L-fucopyranoside 
• 1609693-93-7 Z-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-L-fucopyranoside 
• 1609691-06-6 E-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-D-galactopyranoside 
• 1609691-07-7 E-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-D-galactopyranoside 
• 1609690-98-3 E-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-D-glucopyranoside 
• 1609690-99-4 Z-4-[3-methyl-5-(prop-1-enyl)benzofuran-2-yl]phenyltetra-O-acetyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Acid-mediated intermolecular C-F/C-H cross-coupling of 2-fluorobenzofurans with arenes: Synthesis of 2-arylbenzofurans

Transition-metal-free acid-promoted biaryl construction was achieved via intermolecular C-F/C-H cross-coupling. By treating 2-fluorobenzofurans with arenes in the presence of AlCl3, 2-arylbenzofurans were obtained. This protocol was successfully applied to the short-step orthogonal synthesis of a bioactive 2-arylbenzofuran natural product, which allows independent transformations of C-F and C-Br bonds. Mechanistic studies indicated that α-fluorine-stabilized carbocations, generated via the protonation of 2-fluorobenzofurans, served as key intermediates. The Friedel-Crafts-type C-C bond formation between the α-fluorocarbocations and arenes, followed by hydrogen fluoride elimination, afforded 2-arylbenzofurans. This journal is

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.