N₆-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

Base Information

• Chemical Name: N₆-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]
• CAS No.: 1293390-76-7
• Molecular Formula: C₄₄H₅₆N₉O₁₅P
• Molecular Weight: 981.954

Synonyms:N₆-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

Chemical Property of N₆-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

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Technology Process of N₆-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

There total 5 articles about N₆-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate] 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: 76.0%

N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 5'-[2-(2-nitrophenyl)propyl carbonate] (1293390-69-8) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate] (1293390-76-7)

Guidance literature:

With 1H-tetrazole; In dichloromethane; at 20 ℃; for 22h; Inert atmosphere;

DOI:10.1002/hlca.201000403

Reference yield:

N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (88121-73-7) → N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate] (1293390-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 18 h / 20 °C

2.1: (1S)-10-camphorsulfonic acid / dichloromethane / 18 h / 20 °C / Molecular sieve

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 0.17 h

4.1: pyridine / dichloromethane / 5 h / -30 °C / Inert atmosphere

4.2: 1 h / 20 °C

5.1: 1H-tetrazole / dichloromethane / 22 h / 20 °C / Inert atmosphere

With pyridine; 1H-tetrazole; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/hlca.201000403

Reference yield:

4-methoxy-2,6-dihydropyran (17327-22-9) → N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate] (1293390-76-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (1S)-10-camphorsulfonic acid / dichloromethane / 18 h / 20 °C / Molecular sieve

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 0.17 h

3.1: pyridine / dichloromethane / 5 h / -30 °C / Inert atmosphere

3.2: 1 h / 20 °C

4.1: 1H-tetrazole / dichloromethane / 22 h / 20 °C / Inert atmosphere

With pyridine; 1H-tetrazole; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/hlca.201000403

upstream raw materials:

N₆-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 5'-[2-(2-nitrophenyl)propyl carbonate]

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

4-methoxy-2,6-dihydropyran

N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

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