N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide

Base Information

• Chemical Name: N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide
• CAS No.: 1360157-21-6
• Molecular Formula: C₄₀H₃₈IN₃O₆S
• Molecular Weight: 815.729
• Mol file: 1360157-21-6.mol

Synonyms:N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide

Chemical Property of N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide

There total 2 articles about N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide 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: 85.0%

N,N-bis(2,4-dimethoxybenzyl)-1-trityl-1H-imidazole-4-sulfonamide (1360157-20-5) → N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide (1360157-21-6)

Guidance literature:

N,N-bis(2,4-dimethoxybenzyl)-1-trityl-1H-imidazole-4-sulfonamide; With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; for 0.333333h; Inert atmosphere;

With iodine; In tetrahydrofuran; hexane; at -30 - -5 ℃; for 0.333333h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo2025702

Reference yield:

N,N-bis(2,4-dimethoxybenzyl)-1H-imidazole-4-sulfonamide (1360157-19-2) → N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide (1360157-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.33 h

1.2: 18 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -30 °C / Inert atmosphere

2.2: 0.33 h / -30 - -5 °C / Inert atmosphere

With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo2025702

Reference yield: 53.0%

N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide (1360157-21-6) + 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodo-propionic acid methyl ester (156017-42-4) → (S)-methyl-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,N-bis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)propanoate (1360157-23-8)

Guidance literature:

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodo-propionic acid methyl ester; With iodine; zinc; In N,N-dimethyl-formamide;

N,N-bis(2,4-dimethoxybenzyl)-2-iodo-1-trityl-1H-imidazole-4-sulfonamide; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In N,N-dimethyl-formamide; at 40 ℃; for 2h;

DOI:10.1021/jo2025702

upstream raw materials:

N,N-bis(2,4-dimethoxybenzyl)-1H-imidazole-4-sulfonamide

N,N-bis(2,4-dimethoxybenzyl)-1-trityl-1H-imidazole-4-sulfonamide

Downstream raw materials:

(S)-methyl-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,N-bis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)propanoate