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

Base Information

• Chemical Name: 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)-methylene]-2'-deoxyguanosine
• CAS No.: 1009639-16-0
• Molecular Formula: C₄₂H₄₃N₇O₇
• Molecular Weight: 757.846

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

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

Chemical Property:

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

There total 9 articles about 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N²-[(dimethylamino)-methylene]-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: 89.0%

8-(acetylphenylamino)-N2-[(dimethylamino)methylene]-2'-deoxyguanosine (1009639-15-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N2-[(dimethylamino)-methylene]-2'-deoxyguanosine (1009639-16-0)

Guidance literature:

With pyridine; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201200984

Reference yield:

N-Phenylhydroxylamine (100-65-2) → 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N2-[(dimethylamino)-methylene]-2'-deoxyguanosine (1009639-16-0)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; caesium carbonate; acetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether;

DOI:10.1002/ejoc.201200984

Reference yield:

2'-Deoxyguanosine (961-07-9) → 8-(acetylphenylamino)-5'-O-dimethoxytrityl-N2-[(dimethylamino)-methylene]-2'-deoxyguanosine (1009639-16-0)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1002/ejoc.201200984

upstream raw materials:

N-Phenylhydroxylamine

2'-Deoxyguanosine

N-Phenylacetohydroxamic acid

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

Downstream raw materials:

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

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