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

Base Information

• Chemical Name: 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole
• CAS No.: 26295-44-3
• Molecular Formula: C₂₂H₂₆N₄O₈
• Molecular Weight: 474.47
• Mol file: 26295-44-3.mol

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

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

There total 3 articles about 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-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: 98.0%

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (6205-69-2) + phenylacetylene (536-74-3) → 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole (26295-44-3)

Guidance literature:

With copper(ll) sulfate pentahydrate; C₂₄H₃₅N₇O₇; sodium L-ascorbate; In tetrahydrofuran; water; tert-butyl alcohol; at 30 ℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1002/ejoc.201801714

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-phenyl-1,2,3-triazole (26295-44-3)

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:

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole (26295-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: iron(III) chloride; trimethylsilylazide / dichloromethane / 72 h / 20 °C / Inert atmosphere

2: iron(III) chloride; copper / water; tert-butyl alcohol / 12 h / 20 °C

With iron(III) chloride; trimethylsilylazide; copper; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1039/c1cc13370e

upstream raw materials:

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

phenylacetylene

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

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

Downstream raw materials:

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