70622-68-3

Usage

Uses

Used in Research Contexts:
4'-FORMYLPHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a research compound for exploring its potential biological activities and applications in medicinal chemistry. Its structure and belonging to the glycoside family make it a candidate for studying its interactions with biological systems and possible antibacterial or antiviral properties.
Used in Specialized Industrial Applications:
In specialized industrial applications, 4'-FORMYLPHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE may be utilized for its unique chemical properties or as an intermediate in the synthesis of other complex organic compounds. Its specific use in these applications would depend on the requirements of the industry and the compound's compatibility with other chemicals or processes.

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 7512-17-6 N-Acetyl-D-glucosamine 

Downstream Products

• 135608-51-4 4-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester 
• 135608-53-6 N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-phenoxy)-tetrahydro-pyran-3-yl]-acetamide 
• 135608-52-5 4-(hydroxymethyl)phenyl 3,4,6-tri-O-acetyl-2-(acetamido)-2-deoxy-β-D-glucopyranoside 
• 135608-48-9 N-[(2S,3R,4R,5S,6R)-2-(4-Formyl-phenoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide 
• 135608-50-3 p-carbomethoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Development of specific fluorogenic substrates for human β-N-Acetyl-D-hexosaminidase a for cell-based assays

Inhibitors of human β-N-acetyl-D-hexosaminidase (hHEX) A and human O-GlcNAcase (hOGA) reportedly play roles in multiple diseases, suggesting their potential for pharmacological chaperone (PC) therapy of Sandhoff disease (SD) and Tay-Sachs disease (TSD), as lysosomal storage diseases, and Alzheimer's disease and progressive supranuclear palsy, respectively. In particular, hHEXA inhibitors as PCs have been shown to successfully enhance hHEXA levels, leading to the chronic form of SD and TSD. In the diagnosis of enzyme deficiencies in SD and TSD, artificial hHEXA substrates based on 4-methylumbelliferone as a fluorophore are available and generally used; however, they do not have sufficient performance to screen for potential inhibitors for a PC therapy from compound libraries. Further, there are currently few fluorogenic substrates for hHEXA suitable for such requirements and there are no substrates ideal for cell-based inhibitor screening. Here, we clarified the difference in enzyme active site structure between hHEXA and hOGA from their tertiary structures. To develop lysosome-localized hHEXA-specific fluorogenic substrates based on the difference in their active site structures, our developed quinone methide cleavage substrate design platform was applied for the molecular design of substrates. Thereafter, we synthesized via the shortest route and evaluated novel three-color fluorogenic substrates for hHEXA that exhibited excellent specificity and sensitivity in three human cell lines. The designed substrates represent the first-in-a class of new substrates that can be utilized to screen hHEXA inhibitors in adherent human cultured cells.

Glycosylnaphthalimide-containing fluorescent probe and application thereof

The invention discloses a glycosylnaphthalimide-containing fluorescent probe and application thereof in screening and cell imaging of a glycosidase inhibitor. The structure formula of the glycosylnaphthalimide-containing fluorescent probe is shown as form

Synthesis of N-Acetylglucosamine Aryl β-Glycosides Catalyzed by Crown Compounds

Glycosylation of various phenols with α-D-glucosaminyl chloride peracetate in a solid phase-liquid system catalyzed by crown compounds was studied. The highest yields of aryl β-glycosides were observed at room temperature in acetonitrile using anhydrous p

Glycoconjugated Porphyrins. 3. Synthesis of Flat Amphiphilic Mixed meso-(Glycosylated aryl)porphyrins and Mixed meso-(Glycosylated aryl)alkylporphyrins Bearing Some Mono- and Disaccharide Groups

p-Acetylglycosylated benzaldehydes react with pyrrole by Lindsey's method to produce a variety of flat glycosylated porphyrins.By the same method a large series of amphiphilic mixed glycosylated arylaryl- and mixed glycosylated arylalkylporphyrins have been synthesized, using pyrrole, p-acetylglycosylated benzaldehyde and aryl aldehyde or alkyl aldehyde as starting materials.Under optimized conditions, the di- or teiglycosylated derivatives were principally obtained whereas the formation of meso tetrasubstituted porphyrins is minimized.Deprotection of acetyl glycoside moieties allows us to obtain products with good solubility in neutral aqueous solution and a wide range of amphiphilic character.The structure of these new protected and unprotected compounds in solution was confirmed by 1H NMR studies.

Carbohydrate protein interactions. Syntheses of agglutination inhibitors of wheat germ agglutinin by phase transfer catalysis

Starting from chloride 1, a series of para-substituted aryl 2-acetamido-2-deoxy-β-D-glucopyranosides were prepared using phase transfer catalysis conditions with tetrabutylammonium hydrogen sulfate in 1 M sodium hydroxide and methylene chloride at room temperature.Zemplen de-O-acetylation afforded the unprotected glycosides.Optimization of reaction conditions was evaluated.Several functional group manipulations were effected to widen the number and nature of the para-substituents. Key words: phase transfer catalysis, aryl 2-acetamido-2-deoxy-β-D-glucopyranosides.