121356-12-5

Basic information

• Product Name: (1'-NAPHTHYL) 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: (1'-NAPHTHYL) 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;1-Naphthyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;(1''-NAPHTHYL) 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-SS-D-GLUCOPYRANOSIDE
• CAS NO: 121356-12-5
• Molecular Formula: C₂₄H₂₇NO₉
• Molecular Weight: 473.47248
• Mol File: 121356-12-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 654.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• PKA: 13.45±0.70(Predicted)
• CAS DataBase Reference: (1'-NAPHTHYL) 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1'-NAPHTHYL) 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(121356-12-5)
• EPA Substance Registry System: (1'-NAPHTHYL) 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(121356-12-5)

Safety Data

• Hazardous Substances Data: 121356-12-5(Hazardous Substances Data)

Usage

General Description

"(1'-Naphthyl) 2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-Beta-D-Glucopyranoside" is a complex chemical compound that contains several elements. Its structure involves a naphthyl group as well as an acetamido group and a glucopyranoside group. The “2-acetamido” and "3,4,6-Tri-O-acetyl" portions denote the substitution of certain hydrogen atoms with acetamide and acetyl groups respectively. "2-Deoxy" suggests the absence of an oxygen atom that is present in the original glucose molecule. The "D-Glucopyranoside" part of the name refers to a derivative of glucose, and "beta" indicates the orientation of the glucopyranoside group.

Upstream product

• 10034-19-2 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrochloride 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 90-15-3 α-naphthol 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 

Downstream Products

• 10329-98-3 1-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Design of N-acetyl-6-sulfo-β-D-glucosaminide-based inhibitors of influenza virus sialidase

Biological activity of N-acetyl-6-sulfo-β-D-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/1/71 H3N2). pNP 6-Sulfo-GlcNAc 1a was proved to show substantial activity to inhibit the virus sialidase (IC50=2.8 mM), though p-nitrophenyl (pNP) GlcNAc without 6-sulfo group and pNP 6-sulfo-GlcNH3+ 1b without 2-NHAc showed little activity (IC50 >50 mM). The activity was enhanced nearly 100-fold when the pNP group of 1a was converted to p-acetamidophenyl one 5 (IC50=30 μM) or replaced with 1-naphthyl 6 (IC50=10 μM) or n-propyl one 8 (IC50=11 μM).

Stereospecific Synthesis of Aryl β-D-N-Acetylglucopyranosides by Phase Transfer Catalysis

Under phase transfer catalyzed conditions, 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride (1) reacts with a series of phenoxides to afford high yields of acetylated aryl β-D-N-acetylglucopyranosides (3-8).Deprotection of the hydroxyl g