7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine

Base Information

• Chemical Name: 7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine
• CAS No.: 1448510-88-0
• Molecular Formula: C₆₆H₆₄N₈O₉
• Molecular Weight: 1113.28
• Mol file: 1448510-88-0.mol

Synonyms:7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine

Chemical Property of 7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine

There total 8 articles about 7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine 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: 86.0%

7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-7-deaza-2′-deoxyadenosine (1448510-87-9) + acetic anhydride (108-24-7) → 7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine (1448510-88-0)

Guidance literature:

With pyridine; dmap; triethylamine; at 0 ℃; for 2.5h; Inert atmosphere;

DOI:10.1039/c3ob40842f

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine (1448510-88-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 15 h / 20 °C / Inert atmosphere

2: sodium hydroxide / methanol; water / 12 h / 20 °C / Inert atmosphere

3: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

4: pyridine; dmap; triethylamine / 2.5 h / 0 °C / Inert atmosphere

With 4-methyl-morpholine; pyridine; dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1039/c3ob40842f

Reference yield:

4-amino-5-(prop-2-ynylamino)-7-(5'-(4,4'-dimethoxytrityl)-2'-deoxy-1'-β-D-ribofuranosyl)pyrrolo{2,3-d}pyrimidine (637330-18-8) → 7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-3′-O-acetyl-7-deaza-2′-deoxyadenosine (1448510-88-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

2: pyridine; dmap; triethylamine / 2.5 h / 0 °C / Inert atmosphere

With 4-methyl-morpholine; pyridine; dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1039/c3ob40842f

upstream raw materials:

4-amino-5-(prop-2-ynylamino)-7-(5'-(4,4'-dimethoxytrityl)-2'-deoxy-1'-β-D-ribofuranosyl)pyrrolo{2,3-d}pyrimidine

7-[N-4-(methoxytrityl)-1H-imidazol-5-yl-ethylamino-3-(carbamido)propynyl]-5′-O-(4,4′-dimethoxytrityl)-7-deaza-2′-deoxyadenosine

acetic anhydride

4,4'-dimethoxytrityl chloride