N-[4-acetamido-3-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]amino]phenyl]acetamide

Base Information

• Chemical Name: N-[4-acetamido-3-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]amino]phenyl]acetamide
• CAS No.: 5486-97-5
• Molecular Formula: C15H21N3O6
• Molecular Weight: 347.322
• DSSTox Substance ID: DTXSID50416450
• Wikidata: Q82225745

Synonyms:5486-97-5;DTXSID50416450;AG-F-91423

Chemical Property of N-[4-acetamido-3-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]amino]phenyl]acetamide

Chemical Property:

• Vapor Pressure: 7.28E-22mmHg at 25°C
• Boiling Point: 721.8°Cat760mmHg
• Flash Point: 390.3°C
• Density: 1.545g/cm³
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 339.14303540
• Heavy Atom Count: 24
• Complexity: 463

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=CC(=C(C=C1)NC(=O)C)NC2C(C(C(CO2)O)O)O
• Isomeric SMILES: CC(=O)NC1=CC(=C(C=C1)NC(=O)C)N[C@@H]2[C@@H]([C@H]([C@H](CO2)O)O)O

Technology Process of N-[4-acetamido-3-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]amino]phenyl]acetamide

There total 2 articles about N-[4-acetamido-3-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]amino]phenyl]acetamide 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:

→ Acetic acid (2R,3S,4R)-4-acetoxy-2-acetoxymethyl-6-ethoxy-5-[(E)-hydroxyimino]-tetrahydro-pyran-3-yl ester (5486-97-5,108794-50-9)

Guidance literature:

Aethanol, 3,4,6-Tri-O-acetyl-2-nitroso-α-D-glucopyranosylchlorid (I);

Reference yield:

→ ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-α-D-arabino-hexopyranoside (5486-97-5)

Guidance literature:

aus Tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosylchlorid-dimer/ Methylenchlorid, Ethanol, Δ;

DOI:10.1139/v68-065

Reference yield:

ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-α-D-arabino-hexopyranoside (5486-97-5) → ethyl α-D-glucopyranoside (3198-49-0,15486-24-5,18997-88-1,19467-01-7,34625-23-5,59121-69-6,118245-31-1,118245-32-2,142925-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / triethylamine / methanol; H₂O / 6 h / 4 °C

2: 1.) 1 N HCl, acetaldehyde; 2.) NaBH₄ / 1.) water, 3.5 h, RT; 2.) 30 min, RT, 2 h, water

With hydrogenchloride; sodium tetrahydroborate; acetaldehyde; triethylamine; In methanol; water;

Downstream raw materials:

ethyl α-D-glucopyranoside

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