4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide

Base Information

• Chemical Name: 4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide
• CAS No.: 1001406-59-2
• Molecular Formula: C₁₉H₂₃FN₂O₈
• Molecular Weight: 426.399

Synonyms:4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide

Chemical Property of 4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide

Chemical Property:

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Technology Process of 4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide

There total 6 articles about 4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide 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: 91.0%

N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)-4-nitrobenzamide (1001406-52-5) → 4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide (1001406-59-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; for 3h;

DOI:10.1016/j.bmc.2008.03.038

Reference yield:

(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)amine (249566-74-3) → 4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide (1001406-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 4 h / 20 °C

2: hydrogen; palladium on activated charcoal / tetrahydrofuran; methanol / 3 h / 20 °C

With palladium on activated charcoal; hydrogen; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmc.2017.08.043

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl azide (249566-73-2) → 4-amino-N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide (1001406-59-2)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen; palladium on activated charcoal / tetrahydrofuran; methanol / 1 h / 20 °C

2: triethylamine / tetrahydrofuran / 4 h / 20 °C

3: hydrogen; palladium on activated charcoal / tetrahydrofuran; methanol / 3 h / 20 °C

With palladium on activated charcoal; hydrogen; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmc.2017.08.043

upstream raw materials:

N-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)-4-nitrobenzamide

(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl)amine

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyl azide

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide

Downstream raw materials:

4-(4-{4-[bis(2-chloroethyl)amino]phenyl}butanoylamino)-N-(2-deoxy-2-fluoro-β-D-glucopyranosyl)benzamide

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