N⁶-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine

Base Information

• Chemical Name: N⁶-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine
• CAS No.: 1247023-38-6
• Molecular Formula: C₄₉H₅₅N₈O₈P
• Molecular Weight: 914.998

Synonyms:N⁶-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine

Chemical Property of N⁶-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine

There total 9 articles about N⁶-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine 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: 91.0%

N6-benzoyl-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine (1247023-36-4) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → N6-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine (1247023-38-6)

Guidance literature:

With 4,5-dicyano-1H-imidazole; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2017.01.010

Reference yield:

N6-benzoyladenine (4005-49-6) → N6-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine (1247023-38-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.67 h / 80 - 85 °C

1.2: 0.5 h

2.1: triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 1.5 h / 20 °C

3.1: pyridine / 12 h / 20 °C

4.1: 4,5-dicyano-1H-imidazole / acetonitrile / 2 h / 20 °C

With pyridine; 4,5-dicyano-1H-imidazole; N,O-bis-(trimethylsilyl)-acetamide; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; toluene; acetonitrile;

Reference yield:

5-methyl-2'-O,4'-C-(N-methylaminomethylene)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine → N6-benzoyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine (1247023-38-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 100 °C

1.2: 0.67 h / 100 °C

2.1: triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 1.5 h / 20 °C

3.1: pyridine / 12 h / 20 °C

4.1: 4,5-dicyano-1H-imidazole / acetonitrile / 2 h / 20 °C

With pyridine; 4,5-dicyano-1H-imidazole; N,O-bis-(trimethylsilyl)-acetamide; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; toluene; acetonitrile;

upstream raw materials:

N⁶-benzoyl-5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-O,4'-C-(N-methylaminomethylene)adenosine

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

N₆-benzoyladenine

N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane)-2'-O,4'-C-(N-methylaminomethylene)adenosine

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