1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole

Base Information

• Chemical Name: 1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole
• CAS No.: 1312592-02-1
• Molecular Formula: C₁₇H₂₁N₅O₆
• Molecular Weight: 391.384
• Mol file: 1312592-02-1.mol

Synonyms:1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole

Chemical Property of 1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole

There total 3 articles about 1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole 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: 92.0%

1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole (1312592-17-8) → 1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole (1312592-02-1)

Guidance literature:

1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole; With sodium methylate; In methanol; for 0.5h; pH=9 - 10;

In methanol;

DOI:10.1016/j.carres.2011.03.026

Reference yield:

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (6205-69-2) → 1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole (1312592-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C

2.1: sodium methylate / methanol / 0.5 h / pH 9 - 10

2.2: Dowex-50 (H⁽¹⁺⁾)

With sodium methylate; copper(II) sulfate; sodium L-ascorbate; In methanol; water; tert-butyl alcohol;

DOI:10.1016/j.carres.2011.03.026

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) → 1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole (1312592-02-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium azide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate / dichloromethane; water / 1 h / 20 °C

2.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C

3.1: sodium methylate / methanol / 0.5 h / pH 9 - 10

3.2: Dowex-50 (H⁽¹⁺⁾)

With sodium azide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; copper(II) sulfate; sodium L-ascorbate; In methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/j.carres.2011.03.026

upstream raw materials:

1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole

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

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