5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate)

Base Information

• Chemical Name: 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate)
• CAS No.: 195881-32-4
• Molecular Formula: C₃₉H₄₁N₇O₁₅
• Molecular Weight: 847.792

Synonyms:5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate)

Chemical Property of 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate)

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate)

There total 3 articles about 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate) 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%

succinic acid anhydride (108-30-5) + 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine (195881-24-4) → 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate) (195881-32-4)

Guidance literature:

With 1-methyl-1H-imidazole; In dichloromethane;

DOI:10.1080/07328319708002955

Reference yield:

2-cyano-1-phenylethyl carbonochloridate (195881-17-5) → 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate) (195881-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / pyridine / CH₂Cl₂ / -55 - -10 °C

2: 91 percent / 1-methyl-1H-imidazole / CH₂Cl₂ / 18 h / 20 °C

With pyridine; 1-methyl-1H-imidazole; In dichloromethane;

DOI:10.1002/hlca.200390206

Reference yield:

3-hydroxy-3-phenylpropanenitrile (73627-97-1,121617-17-2,132203-26-0,17190-29-3) → 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate) (195881-32-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / Et₃N, trichloromethyl chloroformate / tetrahydrofuran / 6 h

2: 72 percent / pyridine / 5 h / -60 - -20 °C

3: 91 percent / N-methylimidazole / CH₂Cl₂

With pyridine; 1-methyl-1H-imidazole; triethylamine; trichloromethyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1080/07328319708002955

upstream raw materials:

succinic acid anhydride

5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine

2-cyano-1-phenylethyl carbonochloridate

3-hydroxy-3-phenylpropanenitrile

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