21559-74-0Relevant articles and documents
Synthesis of anti-inflammatory α-and β-linked acetamidopyranosides as inhibitors of toll-like receptor 4 (TLR4)
Wipf, Peter,Eyer, Benjamin R.,Yamaguchi, Yukihiro,Zhang, Feng,Neal, Matthew D.,Sodhi, Chhinder P.,Good, Misty,Branca, Maria,Prindle, Thomas,Lu, Peng,Brodsky, Jeffrey L.,Hackam, David J.
, p. 3097 - 3100 (2015/06/02)
Abstract The low-molecular weight isopropyl 2-acetamido-α-glucoside 16 (C34) inhibits toll-like receptor 4 (TLR4) in enterocytes and macrophages in vitro, and reduces systemic inflammation in mouse models of endotoxemia and necrotizing enterocolitis. We used a copper(II)-mediated solvolysis of anomeric oxazolines and an acid-mediated conversion of β-glucosamine and β-galactosamine pentaacetates to generate analogs of 16 at the anomeric carbon and at C-4 of the pyranose ring. These compounds were evaluated for their influence on TLR4-mediated inflammatory signaling in cultured enterocytes and monocytes. Their efficacy was confirmed using a NF-kB-luciferase reporter mouse, thus establishing the first structure-activity relationship (SAR) study in this series and identifying the more efficacious isopropyl 2-acetamido-α-galactoside 17.
The synthesis of α-glycosides of methyl N-acetylmuramyl-L-alanyl-D-isoglutaminate
Zemlyakov,Kur'yanov,Tsikalov,Chirva
, p. 393 - 397 (2007/10/03)
1-Heptanol, cyclohexanol, and cholesterol were glycosylated with α-glucosaminylchloride peracetate in the presence of HgI2 at 80-90°C to the corresponding peracetylated α-glycosides of N-acetylglucosamine. Successive Zemplen deacetylation, benz
The synthesis of glycosides of 2-acetamido-2-deoxyglucose catalyzed by mercuric iodide
Zemlyakov,Kur'yanov,Sidorova,Chirva
, p. 551 - 558 (2007/10/03)
The glycosylation of various alcohols with peracetylated α-D-glucosaminyl chloride catalyzed with mercuric iodide was studied along with the dependence of the reaction course on temperature, solvent, and quantity of catalyst. At room temperature, only β-glycosides of peracetylated N-acetylglucosamine were shown to result in dichloroethane or nitromethane with high yields. At 90-95°C, anomerization was observed, which led to the corresponding α-glycosides. The possibility of the synthesis of disaccharides with the β1→6 bond catalyzed by mercuric iodide was demonstrated.