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

Base Information

• Chemical Name: N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine
• CAS No.: 155834-50-7
• Molecular Formula: C₂₅H₃₀N₆O₁₀
• Molecular Weight: 574.547

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

Chemical Property of N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine

There total 5 articles about N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 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: 90.0%

4-methoxy-2,6-dihydropyran (17327-22-9) + N6-<2-(4-nitrophenyl)ethoxycarbonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine (111244-87-2) → N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine (155834-50-7)

Guidance literature:

4-methoxy-2,6-dihydropyran; N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine; With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 72h;

With ammonium fluoride; In methanol; at 20 ℃; for 48h;

DOI:10.1002/hlca.200390206

Reference yield:

N6-<2-(4-nitrophenyl)ethoxycarbonyl>-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine (155834-44-9) → N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine (155834-50-7)

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) → N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine (155834-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH*H₂O / CH₂Cl₂ / 5.5 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:

N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine

4-methoxy-2,6-dihydropyran

N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine

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

Downstream raw materials:

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

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

5'-O-(2-dansylethoxycarbonyl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine

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