5'-O-(dimethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine

Base Information

• Chemical Name: 5'-O-(dimethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine
• CAS No.: 156046-17-2
• Molecular Formula: C₄₈H₄₅N₇O₁₄S
• Molecular Weight: 975.99

Synonyms:5'-O-(dimethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine

Chemical Property of 5'-O-(dimethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine

Chemical Property:

Purity/Quality:

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Technology Process of 5'-O-(dimethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine

There total 6 articles about 5'-O-(dimethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>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: 55.0%

2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(dimethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine (156046-16-1) → 5'-O-(dimethoxytrityl)-N6-[2-(4-nitrophenyl)ethoxycarbonyl]adenosine (156046-12-7) + 5'-O-(dimethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine (156046-17-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -5 ℃; for 0.5h;

DOI:10.1002/hlca.19940770104

Reference yield: 7.5%

2-(4-nitro-phenyl)ethanesulfonyl chloride (80259-15-0) + 5'-O-(dimethoxytrityl)-N6-[2-(4-nitrophenyl)ethoxycarbonyl]adenosine (156046-12-7) → 5'-O-(dimethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine (156046-17-2) + 5'-O-(dimethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>-2'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine + 5'-O-(dimethoxytrityl)-N6-<2-(4-nitropehnyl)ethoxycarbonyl>-2',3'-bis-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine

Guidance literature:

With triethylamine; In dichloromethane; chloroform; Ambient temperature; -16 deg C, 15 min, RT, 3 h;

DOI:10.1002/hlca.19950780706

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(dimethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine (156046-17-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / pyridine / 17 h / Ambient temperature

2: 33 percent / 1H-imidazole / pyridine / 26 h / Ambient temperature

3: 98 percent / pyridine / 1.25 h / Ambient temperature

4: 55 percent / Bu₄NF*3H₂O / tetrahydrofuran / 0.5 h / -5 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine;

DOI:10.1002/hlca.19940770104

upstream raw materials:

2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(dimethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>adenosine

2-(4-nitro-phenyl)ethanesulfonyl chloride

5'-O-(dimethoxytrityl)-N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]adenosine

4,4'-dimethoxytrityl chloride

Downstream raw materials:

5'-O-(dimethoxytrityl)-N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-3'-O-[2-(4-nitrophenyl)ethylsulfonyl]adenosine 2'-(2-cyanoethyl N,N-diisopropylphosphoramidite)

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