N⁴-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate

Base Information

• Chemical Name: N⁴-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate
• CAS No.: 121351-62-0
• Molecular Formula: C₄₂H₅₃F₃N₅O₈P
• Molecular Weight: 843.88

Synonyms:N⁴-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate

Chemical Property of N⁴-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate

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Technology Process of N⁴-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate

There total 4 articles about N⁴-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate 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: 82.0%

N,N-diisopropylmethylphosphonamidic chloride (86030-43-5) + N4-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine (109082-28-2) → N4-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate (121351-62-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1h;

DOI:10.1021/ja00200a011

Reference yield:

2'-deoxycytidine monohydrochloride (3992-42-5) → N4-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate (121351-62-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 97.3 percent / aq. NaHSO₃ / 168 h / 37 °C

2: 44 percent / methanol / 24 h

3: 79 percent / pyridine, 4-(dimethylamino)pyridine, triethylamine / 2 h / Ambient temperature

4: 82 percent / diisopropylethylamine / CH₂Cl₂ / 1 h

With pyridine; dmap; sodium hydrogensulfite; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/ja00200a011

Reference yield:

N4-(3-Aminopropyl)-2'-deoxycytidine (109082-26-0) → N4-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine-3'-(O-methyl-N,N-diisopropyl)phosphoramidate (121351-62-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 44 percent / methanol / 24 h

2: 79 percent / pyridine, 4-(dimethylamino)pyridine, triethylamine / 2 h / Ambient temperature

3: 82 percent / diisopropylethylamine / CH₂Cl₂ / 1 h

With pyridine; dmap; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/ja00200a011

upstream raw materials:

N,N-diisopropylmethylphosphonamidic chloride

N⁴-(3-(N-(Trifluoroacetyl)amino)propyl)-5'-dimethoxytrityl-2'-deoxycytidine

2'-deoxycytidine monohydrochloride

N⁴-(3-Aminopropyl)-2'-deoxycytidine

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