N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine

Base Information

• Chemical Name: N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine
• CAS No.: 129944-19-0
• Molecular Formula: C₃₈H₃₅N₅O₇
• Molecular Weight: 673.725

Synonyms:N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine

Chemical Property of N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine

Chemical Property:

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Technology Process of N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine

There total 9 articles about N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine 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: 80.9%

4,4'-dimethoxytrityl chloride (40615-36-9) + N-benzoyl-9-(β-D-ribofuranosyl)-9H-purin-2-amine (129944-18-9) → N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine (129944-19-0)

Guidance literature:

In pyridine; at 20 ℃; for 6h;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2094::AID-HLCA2094>3.0.CO;2-H

Reference yield:

2?amino?9?(β?D?ribofuranosyl)purine (4546-54-7) → N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine (129944-19-0)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; dmap; chloro-trimethyl-silane; triethylamine; In pyridine;

DOI:10.1021/jo00308a003

Reference yield:

6-mercaptoguanosine (85-31-4) → N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine (129944-19-0)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; dmap; chloro-trimethyl-silane; triethylamine; nickel; In pyridine; water;

DOI:10.1021/jo00308a003

upstream raw materials:

4,4'-dimethoxytrityl chloride

N-benzoyl-9-(β-D-ribofuranosyl)-9H-purin-2-amine

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

benzoyl chloride

Downstream raw materials:

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

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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