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

Base Information

• Chemical Name: 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole
• CAS No.: 1312592-17-8
• Molecular Formula: C₂₃H₂₇N₅O₉
• Molecular Weight: 517.495
• Mol file: 1312592-17-8.mol

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

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

There total 2 articles about 1-(2'-acetamido-3',4',6'-tri-O-acetyl-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: 86.0%

N-phenyl propynamide (7341-97-1) + 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (6205-69-2) → 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-(phenylcarbamoyl)-1,2,3-triazole (1312592-17-8)

Guidance literature:

With copper(II) sulfate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20 ℃;

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

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1016/j.carres.2011.03.026

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

upstream raw materials:

N-phenyl propynamide

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

Downstream raw materials:

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