P-AMINOPHENYL-2-ACETAMIDO-2-DEOXY-B-D-GL UCOPYRANOS

Base Information

• Chemical Name: P-AMINOPHENYL-2-ACETAMIDO-2-DEOXY-B-D-GL UCOPYRANOS
• CAS No.: 14419-59-1
• Molecular Formula: C14H20N2O6
• Molecular Weight: 312.323
• Mol file: 14419-59-1.mol

Synonyms:Glucopyranoside,p-aminophenyl 2-acetamido-2-deoxy-, b-D- (8CI);p-Aminophenyl-N-acetyl-b-D-glucosaminide;

Chemical Property of P-AMINOPHENYL-2-ACETAMIDO-2-DEOXY-B-D-GL UCOPYRANOS

Chemical Property:

• Melting Point: 218-221 °C
• Refractive Index: 1.624
• Boiling Point: 670.718 °C at 760 mmHg
• PKA: 12.99±0.70(Predicted)
• Flash Point: 359.437 °C
• PSA: 134.27000
• Density: 1.431 g/cm³
• LogP: -0.43660
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

4-Aminophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Acetylglucosamine derivative; N-acetylglucosamine as the determinant group in artificial antigens.

Technology Process of P-AMINOPHENYL-2-ACETAMIDO-2-DEOXY-B-D-GL UCOPYRANOS

There total 8 articles about P-AMINOPHENYL-2-ACETAMIDO-2-DEOXY-B-D-GL UCOPYRANOS which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-nitrophenyl N-acetyl-β-D-glucosaminide (3459-18-5,50645-66-4) → 4-aminophenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside (14419-59-1,3459-29-8)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 0.166667h; Heating;

Reference yield: 61.8%

p-aminophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-β-D-glucopyranoside (65907-85-9) → 4-aminophenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside (14419-59-1,3459-29-8)

Guidance literature:

With sodium methylate; In methanol; chloroform; acetonitrile; for 1h; Ambient temperature;

DOI:10.1248/cpb.43.266

Reference yield:

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (13089-27-5,13089-23-1) → 4-aminophenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside (14419-59-1,3459-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91.3 percent / H₂ / 10percent Pd/C / ethanol; dioxane / 3 h / 760 Torr / Ambient temperature

2: 61.8 percent / 28percent NaOMe / methanol; acetonitrile; CHCl₃ / 1 h / Ambient temperature

With hydrogen; sodium methylate; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; chloroform; acetonitrile;

DOI:10.1248/cpb.43.266

upstream raw materials:

p-aminophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-β-D-glucopyranoside

4-nitrophenyl N-acetyl-β-D-glucosaminide

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

4-nitro-phenol

Downstream raw materials:

p-Acryloylaminophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside

Refernces

• 1、 Gustafson, Gary R.,Baldino, Carmen M.,O'Donnell, Mary-Margaret E.,Sheldon, Adrian,Tarsa, Robert J.,Verni, Christopher J.,Coffen, David L.. "Incorporation of carbohydrates and peptides into large triazine-based screening libraries using automated parallel synthesis". . p. 4051 - 4065. Retrieved 2007/10/03.
• 2、 Kobayashi, Kazukiyo,Kakishita, Naohito,Okada, Masahiko,Akaike, Toshihiro,Usui, Taichi. "CHEMO-ENZYMATIC SYNTHESIS OF A GLYCOPOLYMER CARRYING CLUSTERED-N-ACETYL-Β-LACTOSAMINE MOIETIES". . p. 753 - 766. Retrieved 2007/10/02.