N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

Base Information

• Chemical Name: N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]
• CAS No.: 1293390-72-3
• Molecular Formula: C₄₂H₅₅N₆O₁₄P
• Molecular Weight: 898.904

Synonyms:N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

Chemical Property of N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

Chemical Property:

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Technology Process of N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

There total 8 articles about N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 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: 98.0%

N4-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 5'-[2-(2-nitrophenyl)propyl carbonate] (1293390-65-4) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → N4-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate] (1293390-72-3)

Guidance literature:

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

DOI:10.1002/hlca.201000403

Reference yield:

3-methyl-1-(phenoxyacetyl)-1H-imidazol-3-ium chloride → N4-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate] (1293390-72-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,1,1,3,3,3-hexamethyl-disilazane / 4 h / Reflux

1.2: 20.5 h / 4 - 20 °C

1.3: 4 h / 20 °C

2.1: pyridine / 18 h / 20 °C

3.1: (1S)-10-camphorsulfonic acid / dichloromethane / 18 h / 20 °C / Molecular sieve

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

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

5.2: 1 h / 20 °C

6.1: 1H-tetrazole / dichloromethane / 20 h / 20 °C

With pyridine; 1H-tetrazole; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/hlca.201000403

Reference yield:

N4-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (1293390-47-2) → N4-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine 3'-(2-cyanoethyl N,N-diisopropylphoshoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate] (1293390-72-3)

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 / 20 h / 20 °C

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

DOI:10.1002/hlca.201000403

upstream raw materials:

N⁴-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

N₄-(phenoxyacetyl)-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)citidine

2-(2-nitrophenyl)propyl chloroformate

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