1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole

Base Information

• Chemical Name: 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole
• CAS No.: 482359-34-2
• Molecular Formula: C₂₄H₂₃N₃O₇
• Molecular Weight: 465.463
• Mol file: 482359-34-2.mol

Synonyms:1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole

Chemical Property of 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole

There total 6 articles about 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole 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: 70.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 4(5)-nitroimidazole cesium salt → 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole (482359-34-2)

Guidance literature:

In tetrahydrofuran; at 62 ℃; for 3h;

DOI:10.1055/s-2002-33505

Reference yield: 68.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 4(5)-nitroimidazole cesium salt → 1-(2'-deoxy-3',5'-di-O-toluoyl-β-D-ribofuranosyl)-4-nitroimidazole + 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole (482359-34-2)

Guidance literature:

In tetrahydrofuran; at 60 ℃; regioselective reaction;

DOI:10.3998/ark.5550190.p010.075

Reference yield:

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose (4330-34-1) → 1-(2'-deoxy-3',5'-di-O-toluoyl-β-D-ribofuranosyl)-4-nitroimidazole + 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-nitroimidazole (482359-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / 0.33 h / 20 °C / Inert atmosphere

1.2: 10 - 15 °C / Inert atmosphere

2.1: tetrahydrofuran / 60 °C

With acetic acid; In tetrahydrofuran;

DOI:10.3998/ark.5550190.p010.075

upstream raw materials:

4⁽⁵⁾-Nitroimidazole sodium salt

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

4⁽⁵⁾-nitroimidazole silver salt

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

Downstream raw materials:

5-amino-4-(2,2-dicyanovinyl)-1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-ribofuranosyl)imidazole

5-amino-1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-ribofuranosyl)imidazole