6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine

Base Information

• Chemical Name: 6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine
• CAS No.: 1585977-31-6
• Molecular Formula: C₄₇H₄₄N₆O₁₀S
• Molecular Weight: 884.967

Synonyms:6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine

Chemical Property of 6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine

Chemical Property:

Purity/Quality:

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Technology Process of 6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine

There total 2 articles about 6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine 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: 52.0%

(4,5-dimethoxy-2-nitrophenyl)methanethiol (1585977-30-5) + N-(9-{5-[bis(4-methoxyphenyl)phenylmethoxyphenyl]-4-hydroxytetrahydrofuran-2-yl}-8-bromo-9H-purin-6-yl)benzamide (129451-79-2) → 6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine (1585977-31-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c3ob42427h

Reference yield:

6-nitroveratrylbromide (53413-67-5) → 6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine (1585977-31-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium thioacetate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

1.2: 12 h / 60 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With potassium carbonate; potassium thioacetate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/c3ob42427h

Reference yield: 77.0%

6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-8-(6-nitroveratrylthio)-2′-deoxyadenosine (1585977-31-6) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-3'-O-(N,N-diisopropyl-β-cyanoethylphosphoramidyl)-8-(6-nitroveratrylthio)-2'-deoxyadenosine (1585977-32-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/c3ob42427h

upstream raw materials:

(4,5-dimethoxy-2-nitrophenyl)methanethiol

N-(9-{5-[bis(4-methoxyphenyl)phenylmethoxyphenyl]-4-hydroxytetrahydrofuran-2-yl}-8-bromo-9H-purin-6-yl)benzamide

6-nitroveratrylbromide

Downstream raw materials:

6-N-benzoyl-5'-O-(4,4′-dimethoxytrityl)-3'-O-(N,N-diisopropyl-β-cyanoethylphosphoramidyl)-8-(6-nitroveratrylthio)-2'-deoxyadenosine

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