2-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside

Base Information

• Chemical Name: 2-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside
• CAS No.: 13264-92-1
• Molecular Formula: C14H18 N2 O8
• Molecular Weight: 342.306
• Hs Code.: 2932990090
• European Community (EC) Number: 236-258-8
• DSSTox Substance ID: DTXSID801196733
• Nikkaji Number: J213.793C
• Wikidata: Q27162471
• Mol file: 13264-92-1.mol

Synonyms:13264-92-1;2-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside;2-Nitrophenyl-N-acetyl-beta-D-glucosaminide;2-Nitrophenyl 2-(acetylamino)-2-deoxy-b-D-Glucopyranoside;N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(2-nitrophenoxy)oxan-3-yl]acetamide;2-Nitrophenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside;EINECS 236-258-8;2-nitrophenyl N-acetyl-beta-D-glucosaminide;o-nitrophenyl N-acetyl-beta-D-glucosaminide;N-((2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(2-nitrophenoxy)tetrahydro-2H-pyran-3-yl)acetamide;SCHEMBL1034614;CHEBI:90334;2-Nitrophenyl2-(acetylamino)-2-deoxy-b-D-Glucopyranoside;DTXSID801196733;MFCD00067648;AKOS002688246;CS-0444579;Q27162471;2-Nitrophenyl 2-(acetylamino)-2-deoxy--D-glucopyranoside

Chemical Property of 2-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Melting Point: 176-177oC
• Boiling Point: 685.2 °C at 760 mmHg
• PKA: 12.84±0.70(Predicted)
• Flash Point: 368.2 °C
• PSA: 154.07000
• Density: 1.51 g/cm³
• LogP: -0.16860
• Storage Temp.: 2-8°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 342.10631554
• Heavy Atom Count: 24
• Complexity: 457

Purity/Quality:

99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2=CC=CC=C2[N+](=O)[O-])CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC=CC=C2[N+](=O)[O-])CO)O)O

Technology Process of 2-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside

There total 7 articles about 2-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside 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: 64.0%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + 2-hydroxynitrobenzene (88-75-5,78813-12-4) → o-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (13264-92-1,152957-34-1)

Guidance literature:

N-Acetyl-D-glucosamine; 2-hydroxynitrobenzene; With triethylamine; In water; at 20 ℃; for 0.166667h; Sealed tube;

With 2-chloro-1,3-dimethylimidazolinium chloride; In water; at -10 - 80 ℃; for 3h; Microwave irradiation; Sealed tube;

DOI:10.1039/d0ob01727b

Reference yield:

o-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (13089-26-4,13264-91-0) → o-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (13264-92-1,152957-34-1)

Guidance literature:

With methanol; chloroform; sodium methylate;

DOI:10.1039/jr9570004754

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → o-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside (13264-92-1,152957-34-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 g / KH; 18-crown-6 / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 18.4 g / K₂CO₃ / methanol; H₂O / 20 °C

With 18-crown-6 ether; potassium hydride; potassium carbonate; In methanol; dichloromethane; water;

DOI:10.1016/S0008-6215(02)00470-6

upstream raw materials:

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

2-hydroxynitrobenzene

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrochloride

Downstream raw materials:

isopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside

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