4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole

Base Information

• Chemical Name: 4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole
• CAS No.: 74134-93-3
• Molecular Formula: C₁₃H₁₅N₃O₄
• Molecular Weight: 277.28
• Mol file: 74134-93-3.mol

Synonyms:4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole

Chemical Property of 4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole

There total 9 articles about 4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole 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: 100.0%

2-phenyl-4-(2,3-O-isopropylidene-β-D-ribosyl)-2H-1,2,3-triazole (74134-96-6) → 4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole (74134-93-3)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 24h;

DOI:10.1021/acs.joc.6b00323

Reference yield:

3,6-anhydro-D-allo-2-heptulose phenylosazone (21090-79-9,21238-55-1,73364-68-8,73364-69-9,73364-70-2,73364-71-3) → 4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole (74134-93-3)

Guidance literature:

With copper(II) sulfate; In methanol; propan-1-ol; water; for 3h; Heating;

DOI:10.1016/S0008-6215(00)86026-7

Reference yield:

1,5-O-diacetyl-2,3-O-isopropylidene-D-ribofuranoside (141979-56-8) → 4-β-D-arabinofuranosyl-2-phenyl-1,2,3-osotriazole (74134-93-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: indium / 1,2-dichloro-ethane / 6 h / 90 °C / Inert atmosphere; Sealed tube

1.2: 5 h / 20 °C

2.1: potassium carbonate / methanol / 8 h / 20 °C

3.1: 1H-imidazole; dmap / acetonitrile / 2 h / 20 °C

4.1: copper(l) iodide; trimethylsilylazide / N,N-dimethyl-formamide; ethanol / 0.5 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation

5.1: bis(η3-allyl-μ-chloropalladium(II)); 2-(di-1-adamantylphosphino)-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl; potassium phosphate / toluene / 10 h / 120 °C / Sealed tube; Inert atmosphere

6.1: cesium fluoride; tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 50 °C

7.1: trifluoroacetic acid; water / dichloromethane / 24 h / 0 - 20 °C

With 1H-imidazole; dmap; indium; potassium phosphate; copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); trimethylsilylazide; 2-(di-1-adamantylphosphino)-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl; tetrabutyl ammonium fluoride; water; potassium carbonate; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/acs.joc.6b00323

upstream raw materials:

3,6-anhydro-D-allo-2-heptulose phenylosazone

2-phenyl-4-(2,3-O-isopropylidene-β-D-ribosyl)-2H-1,2,3-triazole

2,3-O-isopropylidene-D-ribofuranose

1,5-O-diacetyl-2,3-O-isopropylidene-D-ribofuranoside

Downstream raw materials:

2-phenyl-4-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-1,2,3-osotriazole