21559-74-0

Upstream product

• 108-93-0 cyclohexanol 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 297132-68-4 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate 
• 108-24-7 acetic anhydride 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 

Downstream Products

• 624738-78-9 (R)-4-{(S)-2-[(R)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-cyclohexyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 624738-69-8 (R)-4-{(S)-2-[(R)-2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-cyclohexyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 624738-74-5 cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-α-D-glucopyranoside 
• 509086-48-0 cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 
• 21559-73-9 cyclohexyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of anti-inflammatory α-and β-linked acetamidopyranosides as inhibitors of toll-like receptor 4 (TLR4)

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.

New α-selective thermal glycosylation of acetyl-protected 2-acetamido-2-deoxy-β-D-glucopyranosyl diphenylphosphinate

This paper describes new α-selective thermal glycosylation using acetyl-protected 2-acetamido-2-deoxy-β-D-glucopyranosyl diphenylphosphinate (4) as a glycosyl donor. When the glycosylation of 4 with 1-hexanol was carried out under various conditions, the conditions using trimethylsilyl trifluoromethanesulfonate as a promoter in nitromethane at reflux temperature were most suitable for the formation of the α anomer. The glycosylation of 4 with the other common alcohols gave corresponding α-glycosides in relatively high yields under the conditions. When cholesterol, a very steric hindered alcohol, was used as a glycosyl acceptor, α-glycoside was also produced predominantly. Copyright (C) 2000 Elsevier Science Ltd.

The synthesis of glycosides of 2-acetamido-2-deoxyglucose catalyzed by mercuric iodide

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.

The synthesis of α-glycosides of methyl N-acetylmuramyl-L-alanyl-D-isoglutaminate

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

Use of sodium iodide and crown ether in the synthesis of N-acetylglucosamine glycosides

A pair of sodium iodide-crown ether reagents was used in the synthesis of N-acetylglucosamine glycosides. At room temperature, the reaction resulted in β-glycosides, whereas at 85-90°C, it gave a mixture of anomers or α-anomer only.

Studies of the stereoselective reduction of 2-hydroxyimino- hexopyranosides: LiBH4-Me3SiCl, a mild reducing agent of oximes to amines

Reduction of the title compounds of types 1 and 2 under mild conditions using LiBH4-Me3SiCl species, followed by acetylation, yielded the corresponding 2-amino sugars of α-D-gluco (5) and β D-manno (6) configuration, respectively, wi