8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Base Information

• Chemical Name: 8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine
• CAS No.: 1009639-11-5
• Molecular Formula: C₃₀H₄₈N₆O₅Si₂
• Molecular Weight: 628.919

Synonyms:8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Chemical Property of 8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

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Technology Process of 8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

There total 5 articles about 8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 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: 73.0%

O6-(benzotriazol-1-yl)-3′,5′-di-O-(t-butyldimethylsilyl)-2′-deoxyguanosine (1009639-09-1) + N-Phenylacetohydroxamic acid (1795-83-1) → 8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (1009639-11-5)

Guidance literature:

With caesium carbonate; In 1,2-dimethoxyethane; at 20 ℃;

DOI:10.1055/s-2007-990913

Reference yield:

2'-Deoxyguanosine (961-07-9) → 8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (1009639-11-5)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; 1H-imidazole; caesium carbonate; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201200984

Reference yield:

3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (51549-35-0) → 8-[acetyl(phenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (1009639-11-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With caesium carbonate; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201200984

upstream raw materials:

O⁶-(benzotriazol-1-yl)-3′,5′-di-O-(t-butyldimethylsilyl)-2′-deoxyguanosine

N-Phenylacetohydroxamic acid

2'-Deoxyguanosine

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

Downstream raw materials:

8-[acetyl(phenyl)amino]-2'-deoxyguanosine

8-(acetylphenylamino)-N²-[(dimethylamino)methylene]-2'-deoxyguanosine

8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)-methylene]-2'-deoxyguanosine

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

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