N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Base Information

• Chemical Name: N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)
• CAS No.: 129944-21-4
• Molecular Formula: C₅₃H₆₆N₇O₈PSi
• Molecular Weight: 988.208

Synonyms:N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Chemical Property of N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)

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Technology Process of N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)

There total 13 articles about N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 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: 98.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N2-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine (129944-20-3) → N2-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) (129944-21-4)

Guidance literature:

With 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1021/jo00308a003

Reference yield:

2?amino?9?(β?D?ribofuranosyl)purine (4546-54-7) → N2-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) (129944-21-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) chlorotrimethylsilane, pyridine / 1) 15 min, 25 deg C, 2) 2 h

2: (dimethylamino)pyridine, triethylamine / pyridine / 12 h / 0 °C

3: 45 percent / imidazole / pyridine / 5 h / 0 °C

4: 98 percent / diisopropylethylamine, N-methylimidazole / tetrahydrofuran / 1 h / 25 °C

With pyridine; 1H-imidazole; 1-methyl-1H-imidazole; dmap; chloro-trimethyl-silane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine;

DOI:10.1021/jo00308a003

Reference yield:

6-mercaptoguanosine (85-31-4) → N2-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) (129944-21-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / Raney-Ni / H₂O / 2 h / Heating

2: 1) chlorotrimethylsilane, pyridine / 1) 15 min, 25 deg C, 2) 2 h

3: (dimethylamino)pyridine, triethylamine / pyridine / 12 h / 0 °C

4: 45 percent / imidazole / pyridine / 5 h / 0 °C

5: 98 percent / diisopropylethylamine, N-methylimidazole / tetrahydrofuran / 1 h / 25 °C

With pyridine; 1H-imidazole; 1-methyl-1H-imidazole; dmap; chloro-trimethyl-silane; triethylamine; N-ethyl-N,N-diisopropylamine; nickel; In tetrahydrofuran; pyridine; water;

DOI:10.1021/jo00308a003

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine

N²,O^2',O^3',O^5'-tetrabenzoylguanosine

4,4'-dimethoxytrityl chloride

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