5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N⁶-methyl-N⁶-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine

Base Information

• Chemical Name: 5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N⁶-methyl-N⁶-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine
• CAS No.: 644990-28-3
• Molecular Formula: C₄₁H₄₇N₇O₁₄S
• Molecular Weight: 893.929

Synonyms:5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N⁶-methyl-N⁶-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine

Chemical Property of 5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N⁶-methyl-N⁶-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine

Chemical Property:

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Technology Process of 5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N⁶-methyl-N⁶-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine

There total 4 articles about 5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N⁶-methyl-N⁶-{[2-(4-mitrophenyl)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: 54.0%

2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethyl carbonochloride hydrochloride + N6-methyl-N6-{[2-(4-nitropheyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine (644990-32-9) → 5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N6-methyl-N6-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine (644990-28-3)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1002/hlca.200390205

Reference yield:

N6-methyl-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (161001-99-6) → 5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N6-methyl-N6-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine (644990-28-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / pyridine / 72 h

2: 81 percent / TsOH*H₂O / CH₂Cl₂ / 7 h

3: 91 percent / nBu₄NF / tetrahydrofuran

4: 54 percent / pyridine / 0 °C

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

DOI:10.1002/hlca.200390205

Reference yield:

N6-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine (644990-25-0) → 5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N6-methyl-N6-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine (644990-28-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / TsOH*H₂O / CH₂Cl₂ / 7 h

2: 91 percent / nBu₄NF / tetrahydrofuran

3: 54 percent / pyridine / 0 °C

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

DOI:10.1002/hlca.200390205

upstream raw materials:

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

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

N⁶-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine

N⁶-methyl-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine

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