70622-68-3

Basic information

• Product Name: 4'-FORMYLPHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: 4-Formylphenyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;4''-FORMYLPHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-SS-D-GLUCOPYRANOSIDE;4'-FORMYLPHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• CAS NO: 70622-68-3
• Molecular Formula: C₂₁H₂₅NO₁₀
• Molecular Weight: 451.4239
• Mol File: 70622-68-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 640.6 °C at 760 mmHg
• Flash Point: 341.2 °C
• Appearance: /
• Density: 1.32g/cm³
• CAS DataBase Reference: 4'-FORMYLPHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-FORMYLPHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(70622-68-3)
• EPA Substance Registry System: 4'-FORMYLPHENYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(70622-68-3)

Safety Data

• Hazardous Substances Data: 70622-68-3(Hazardous Substances Data)

Usage

General Description

"4'-Formylphenyl 2-Acetamido-3,4,6-Tri-O-acetyl-2-deoxy-beta-D-glucopyranoside" is a complex synthetic organic compound which is a derivative of glucopyranoside. This particular compound has a formylphenyl group at the 4' position and several acetyl groups attached to it. Its structure suggests it belongs to the glycoside family, which is known for its extensive range of biological activities. Glycosides are commonly used in medicinal chemistry and could potentially showcase antibacterial or antiviral activities. However, specific information about the pharmacological properties or potential applications of this particular chemical is not readily available, suggesting its use may largely be limited to research contexts or specialized industrial applications.

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

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

Relevant articles and documents

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.

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

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.