5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole

Base Information

• Chemical Name: 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole
• CAS No.: 1444827-58-0
• Molecular Formula: C₂₄H₂₅N₃O₁₂S
• Molecular Weight: 579.541

Synonyms:5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole

Chemical Property of 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole

Chemical Property:

Purity/Quality:

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Technology Process of 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole

There total 5 articles about 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 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: 46.0%

→ 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole (1444827-58-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 60 ℃; for 16h;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole (1444827-58-0)

Guidance literature:

Multi-step reaction with 4 steps

1: tetra-(n-butyl)ammonium iodide

2: ammonia / toluene / 16 h / 20 °C

3: dichloromethane / 3 h / 20 °C / Inert atmosphere

4: triethylamine / tetrahydrofuran / 16 h / 60 °C

With ammonia; tetra-(n-butyl)ammonium iodide; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jm400723n

Reference yield:

2-chloro-1-(4-nitrophenyl)ethanone (34006-49-0) + 2-[(2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino]-4-dimethylamino-1,3-thiazabuta-1,3-diene (1444827-52-4) → 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole (1444827-58-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 60 ℃; for 16h;

DOI:10.1021/jm400723n

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate

2-chloro-1-(4-nitrophenyl)ethanone

2-[(2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino]-4-dimethylamino-1,3-thiazabuta-1,3-diene

N-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)thiourea

Downstream raw materials:

5-p-nitrobenzoyl-2-((α-D-mannopyranos-1-yl)amino)thiazole

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