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

Base Information

• Chemical Name: 5'-O-[(2-cyano-1-pheylethoxy)carbonyl]-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine
• CAS No.: 195881-22-2
• Molecular Formula: C₃₄H₃₇N₅O₁₃
• Molecular Weight: 723.693

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

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

Chemical Property:

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

There total 3 articles about 5'-O-[(2-cyano-1-pheylethoxy)carbonyl]-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine 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: 58.0%

N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytosine (155834-52-9) + 2-cyano-1-phenylethyl carbonochloridate (195881-17-5) → 5'-O-[(2-cyano-1-pheylethoxy)carbonyl]-N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine (195881-22-2) + 3'-O-[(2-cyano-1-pheylethoxy)carbonyl]-N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine + 3',5'-bis-O-[(2-cyano-1-pheylethoxy)carbonyl]-N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine

Guidance literature:

With pyridine; at -60 - -20 ℃; for 5h;

DOI:10.1080/07328319708002955

Reference yield:

4-methoxy-2,6-dihydropyran (17327-22-9) → 5'-O-[(2-cyano-1-pheylethoxy)carbonyl]-N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine (195881-22-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 48 h / 20 °C

1.2: 85 percent / NH₄F / methanol / 72 h / 20 °C

2.1: 58 percent / pyridine / CH₂Cl₂ / -60 - -20 °C

With pyridine; pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1002/hlca.200390206

Reference yield:

N4-<2-(4-nitrophenyl)ethoxycarbonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (155834-43-8) → 5'-O-[(2-cyano-1-pheylethoxy)carbonyl]-N4-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine (195881-22-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 48 h / 20 °C

1.2: 85 percent / NH₄F / methanol / 72 h / 20 °C

2.1: 58 percent / pyridine / CH₂Cl₂ / -60 - -20 °C

With pyridine; pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1002/hlca.200390206

upstream raw materials:

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

2-cyano-1-phenylethyl carbonochloridate

4-methoxy-2,6-dihydropyran

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

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