Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4-tri-O-acetyl-beta-D-glucopyranuronate

Base Information

• Chemical Name: Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4-tri-O-acetyl-beta-D-glucopyranuronate
• CAS No.: 221287-92-9
• Molecular Formula: C23H23 N3 O13 S
• Molecular Weight: 581.51
• DSSTox Substance ID: DTXSID101108808
• Mol file: 221287-92-9.mol

Synonyms:221287-92-9;Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4- tri-O-acetyl-beta-D-glucopyranuronate;DTXSID101108808;Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4-tri-O-acetyl-beta-D-glucopyranuronate;beta-D-Glucopyranosiduronic acid, 2-[[(5-nitro-2-thiazolyl)amino]carbonyl]phenyl, methyl ester, 2,3,4-triacetate;methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy]oxane-2-carboxylate;Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4- tri-O-acetyl- beta -D-glucopyranuronate

Chemical Property of Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4-tri-O-acetyl-beta-D-glucopyranuronate

Chemical Property:

• Melting Point: 268-270°C
• Refractive Index: 1.597
• PSA: 250.71000
• Density: 1.515g/cm³
• LogP: 2.27330
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO, Methanol
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 12
• Exact Mass: 581.09515897
• Heavy Atom Count: 40
• Complexity: 992

Purity/Quality:

97% ^*data from raw suppliers

Methyl1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4-tri-O-acetyl-β-D-glucopyranuronate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=CC=CC=C2C(=O)NC3=NC=C(S3)[N+](=O)[O-])C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OC2=CC=CC=C2C(=O)NC3=NC=C(S3)[N+](=O)[O-])C(=O)OC)OC(=O)C

Technology Process of Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4-tri-O-acetyl-beta-D-glucopyranuronate

There total 4 articles about Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4-tri-O-acetyl-beta-D-glucopyranuronate 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: 67.0%

2-amino-5-nitro-1,3-thiazole (121-66-4,176384-36-4,8023-00-5) + methyl 1-(2-carboxyphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (221287-90-7) → methyl 1-<2-N-(5-nitrothiazol-2-yl)carboxamido>phenyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (221287-92-9)

Guidance literature:

With dmap; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; a) 20 deg C, 2 h, b) 0 deg C, 16 h;

DOI:10.1039/a806676k

Reference yield:

benzyl salicylate (118-58-1) → methyl 1-<2-N-(5-nitrothiazol-2-yl)carboxamido>phenyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (221287-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / Ag₂O, isoquinoline / 1 h / 20 °C

2: 80 percent / cyclohexene / Pd/C / propan-2-ol / 0.5 h / Heating

3: 67 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 4-N,N-dimethylaminopyridine, 1-hydroxybenzotriazole monohydrate / dimethylformamide / a) 20 deg C, 2 h, b) 0 deg C, 16 h

With isoquinoline; dmap; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; cyclohexene; palladium on activated charcoal; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1039/a806676k

Reference yield:

methyl 1-<2-(benzyloxycarbonyl)phenyl>-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (221287-88-3) → methyl 1-<2-N-(5-nitrothiazol-2-yl)carboxamido>phenyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (221287-92-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / cyclohexene / Pd/C / propan-2-ol / 0.5 h / Heating

2: 67 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 4-N,N-dimethylaminopyridine, 1-hydroxybenzotriazole monohydrate / dimethylformamide / a) 20 deg C, 2 h, b) 0 deg C, 16 h

With dmap; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cyclohexene; palladium on activated charcoal; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1039/a806676k

upstream raw materials:

2-amino-5-nitro-1,3-thiazole

methyl 1-(2-carboxyphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

benzyl salicylate

methyl 1-<2-(benzyloxycarbonyl)phenyl>-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

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