O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite

Base Information

• Chemical Name: O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite
• CAS No.: 1009639-17-1
• Molecular Formula: C₅₁H₆₀N₉O₈P
• Molecular Weight: 958.067

Synonyms:O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite

Chemical Property of O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite

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Technology Process of O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite

There total 10 articles about O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite 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: 85.0%

2-cyanoethyl bis(diisopropylamino)phosphite + 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N2-[(dimethylamino)-methylene]-2'-deoxyguanosine (1009639-16-0) → O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N2-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite (1009639-17-1)

Guidance literature:

With 4,5-dicyano-1H-imidazole; In dichloromethane; acetonitrile; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201200984

Reference yield:

N-Phenylhydroxylamine (100-65-2) → O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N2-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite (1009639-17-1)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydrogencarbonate / diethyl ether / 0 °C

2: caesium carbonate / 1,2-dimethoxyethane / 20 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran

4: pyridine / 20 °C / Inert atmosphere

5: pyridine / 20 °C / Inert atmosphere

6: 4,5-dicyano-1H-imidazole / dichloromethane; acetonitrile / 20 °C / Inert atmosphere

With pyridine; 4,5-dicyano-1H-imidazole; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; caesium carbonate; acetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201200984

Reference yield:

2'-Deoxyguanosine (961-07-9) → O-(2-cyanoethyl)-N,N-diisopropyl 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N2-[(dimethylamino)methylene]-2'-deoxyguanosine-3'-phosphoramidite (1009639-17-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1H-imidazole; pyridine / 18 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 14 h / 20 °C

3: caesium carbonate / 1,2-dimethoxyethane / 20 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran

5: pyridine / 20 °C / Inert atmosphere

6: pyridine / 20 °C / Inert atmosphere

7: 4,5-dicyano-1H-imidazole / dichloromethane; acetonitrile / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 4,5-dicyano-1H-imidazole; tetrabutyl ammonium fluoride; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.201200984

upstream raw materials:

N-Phenylhydroxylamine

2'-Deoxyguanosine

N-Phenylacetohydroxamic acid

3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

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