21588-60-3

Upstream product

• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 108-93-0 cyclohexanol 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 1454311-01-3 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)benzotriazole 
• 108-24-7 acetic anhydride 
• 14131-68-1 N-acetyl-D-glucosamine 
• 2873-29-2 D-glucal triacetate 
• 257294-52-3 cyclohexyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 851771-55-6 cyclohexyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 297132-68-4 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 

Downstream Products

• 21559-72-8 cyclohexyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 500768-00-3 cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-β-D-glucopyranoside 
• 500768-01-4 (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-cyclohexyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 624738-12-1 (R)-4-{(S)-2-[(R)-2-((4aR,6R,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 
• 211567-30-5 cyclohexyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 
• 211567-24-7 Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-7-acetylamino-6-cyclohexyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 211567-33-8 Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine 
• 211567-23-6 cyclohexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 211567-27-0 N-((2R,4aR,6R,7R,8S,8aS)-6-Cyclohexyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 175469-68-8 Benzoic acid 2-[(3aR,4S,6S,7S,7aR)-6-((4aR,6R,7R,8R,8aS)-7-acetylamino-6-cyclohexyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-ethyl ester 
• 175469-69-9 N-{(4aR,6R,7R,8R,8aS)-6-Cyclohexyloxy-8-[(3aR,4S,6S,7S,7aR)-7-(2-hydroxy-ethoxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide 
• 197575-01-2 (R)-2-((4aR,6R,7R,8R,8aS)-7-Acetylamino-6-cyclohexyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 
• 197574-97-3 N-((4aR,6R,7R,8R,8aS)-6-Cyclohexyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 

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.

Glycosylated derivatives of substituted hydroxylamine. II. the phase transfer synthesis and the study of the glycosyl transfer reaction of glucosaminides of substituted hydroxylamine

The interaction of 1-(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-β-D- glucopyranosyloxy)benzotriazole with primary and secondary aliphatic and cycloaliphatic alcohols or diisopropylidenegalactose in refluxing methylene chloride under the catalysis of Lewis a

H2so4-silica promoted direct formation of β-glycosides of N-Acetyl glycosylamines under microwave conditions

N-Acetyl glycosamines are important building blocks for the synthesis of biologically active oligosaccharides. This communication describes a simple direct protocol for the synthesis of βglycosides of N-acetyl glycosylamines from easily accessible perO-ac

Direct formation of β-glycosides of N-acetyl glycosamines mediated by rare earth metal triflates

A direct, mild and efficient protocol for the preparation of β-glycosides of N-acetyl glucosamine (GlcNAc) and N-acetyl galactosamine (GalNAc) has been developed using peracetylated β-GlcNAc and β-GalNAc as donors. All rare Earth metal triflate promoters

A practical method for preparation of β-glycosides of N-acetylglucosamine

A mild and efficient method for preparation of GlcNAc derivatives by reaction of glycosyl acceptors with glycosyl oxazolines has been developed. The key feature is use of Yb(OTf)3 as promoter, requiring moderate reaction times and equivalence s

Copper(II)-mediated activation of sugar oxazolines: Mild and efficient synthesis of β-glycosides of N-acetylglucosamine

2-Methyl-(3,4,6-tri- O-acetyl- 1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline (5) was reacted with glycosyl acceptors bearing primary (6, 8, 10, 20) or secondary hydroxy groups (12, 14, 16, 18) in the presence of anhydrous cupric bromide or cupric chloride at elevated temperature to provide 2-acet-amido-2-deoxy-β-D-glucopyranosides in 36-92% yield. The reaction conditions are milder than those previously described for oxazoline activation employing p-toluenesulfonic acid or ferric chloride. Treatment of the oxazoline with trimethylsilyl azide (22) and CuCl2 leads to 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (23) in 69% yield. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

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.

Chemical synthesis of N-acetylglucosamine derivatives and their use as glycosyl acceptors by the Mesorhizobium loti chitin oligosaccharide synthase NodC

Rhizobial bacteria synthesize lipo-chitin oligosaccharide signal molecules (Nod factors) that are essential for the formation of symbiotic organs on the roots of host plants, a process known as nodulation. Biosynthesis of the chitin oligosaccharide moiety

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.

Alkylating agents from sugars. Cyclophosphamides derived from 2-amino- 2-deoxy-D-allose

Cyclophosphamides derived from alkyl 2-amino-4,6-O-benzylidene-2-deoxy- β-D-allopyranosides have been synthesized with good yield by treatment of the corresponding 2-amino-2-deoxy-D-allose derivatives with bis(2- chloroethyl)phosphoramide dichloride. The ring-forming reaction took place with very high diastereoselectivity. Subsequent hydrogenolysis gave excellent yields of cyclophosphamides derived from alkyl 2-amino-2-deoxy-β-D- allopyranosides, with hydrophilicity greater than that of the precursors. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose.