4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole

Base Information

• Chemical Name: 4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole
• CAS No.: 161359-23-5
• Molecular Formula: C₂₉H₂₄N₄O₁₁S
• Molecular Weight: 636.596

Synonyms:4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole

Chemical Property of 4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole

Chemical Property:

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Technology Process of 4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole

There total 2 articles about 4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole 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: 39.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (70832-64-3) + 4(5)-nitro-5(4)-sulphonamidoimidazole (6963-63-9) → 4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole (161359-24-6) + 4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole (161359-23-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 16h; 0 deg C -> room temperature;

DOI:10.1080/15257779508012383

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 4(5)-nitro-imidazole-5(4)-sulfonamide (6963-63-9) → 4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole (161359-24-6) + 4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole (161359-23-5)

Guidance literature:

With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction. Yields of byproduct given; 1.) xylene, reflux, 2.) xylene, MeCN, 0 deg C to r.t., 16 h;

DOI:10.1016/0040-4039(94)85344-4

Reference yield: 89.0%

4-nitro-5-sulphonoamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole (161359-23-5) → 4-amino-5-sulfonamido-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)imidazole

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; under 760 Torr;

DOI:10.1016/0040-4020(96)00472-3

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

4⁽⁵⁾-nitro-imidazole-5⁽⁴⁾-sulfonamide

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

4⁽⁵⁾-nitro-5⁽⁴⁾-sulphonamidoimidazole

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