N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine

Base Information

• Chemical Name: N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine
• CAS No.: 155834-52-9
• Molecular Formula: C₂₄H₃₀N₄O₁₁
• Molecular Weight: 550.522

Synonyms:N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine

Chemical Property of N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine

Chemical Property:

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Technology Process of N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine

There total 5 articles about N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine 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: 85.0%

4-methoxy-2,6-dihydropyran (17327-22-9) + N4-<2-(4-nitrophenyl)ethoxycarbonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (155834-43-8) → N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine (155834-52-9)

Guidance literature:

4-methoxy-2,6-dihydropyran; N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine; With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 48h;

With ammonium fluoride; In methanol; at 20 ℃; for 72h;

DOI:10.1002/hlca.200390206

Reference yield:

N4-<2-(4-nitrophenyl)ethoxycarbonyl>-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (155834-46-1) → N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine (155834-52-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; acetic acid; for 1.5h; Yield given; Ambient temperature;

DOI:10.1002/hlca.19940770209

Reference yield:

4-methoxy-2,6-dihydropyran (17327-22-9) → N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine (155834-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH*H₂O / CH₂Cl₂ / 10 h / Ambient temperature

2: Bu₄NF*3H₂O / tetrahydrofuran; acetic acid / 1.5 h / Ambient temperature

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1002/hlca.19940770209

upstream raw materials:

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

4-methoxy-2,6-dihydropyran

N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>cytidine

Downstream raw materials:

5'-O-[(2-cyano-1-pheylethoxy)carbonyl]-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine 3'-(hydrogen butanedioate)

5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine 3'-2-(4-nitrophenyl)ethyl diisopropylphosphoramidite

N₄-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine 5'-[2-(2-nitrophenyl)propyl carbonate]

N₄-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 5'-[2-(2-nitrophenyl)propyl carbonate]

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