N⁶-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine

Base Information

• Chemical Name: N⁶-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine
• CAS No.: 126616-53-3
• Molecular Formula: C₄₁H₄₅N₅O₅Si
• Molecular Weight: 715.924

Synonyms:N⁶-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine

Chemical Property of N⁶-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine

There total 3 articles about N⁶-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-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: 31.0%

N-(9-{(3aR,4R,6R,6aR)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-tetrahydro-furan-3-ylmethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-benzamide (126616-49-7) + N6-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine (126616-48-6) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8) → N6-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine (126616-53-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; a) 15 min b) 5 h;

DOI:10.1021/jo00297a034

Reference yield:

N6-benzoyl-2',3'-isopropylidene-5'-(2-hydroxytetrahydrofuran-3-yl)-5'-deoxyadenosine (126616-46-4) → N6-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine (126616-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 39 percent / imidazole / dimethylformamide; hexamethylphosphoric acid triamide / 1.33 h / 50 °C

2: 31 percent / potassium tert-butoxide / tetrahydrofuran / -78 °C / a) 15 min b) 5 h

With 1H-imidazole; potassium tert-butylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide;

DOI:10.1021/jo00297a034

Reference yield:

N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine (85681-04-5) → N6-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine (126616-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / DIBAL / tetrahydrofuran; toluene / 3 h / -78 °C

2: 39 percent / imidazole / dimethylformamide; hexamethylphosphoric acid triamide / 1.33 h / 50 °C

3: 31 percent / potassium tert-butoxide / tetrahydrofuran / -78 °C / a) 15 min b) 5 h

With 1H-imidazole; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00297a034

upstream raw materials:

N-(9-{(3aR,4R,6R,6aR)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-tetrahydro-furan-3-ylmethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-benzamide

N⁶-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine

dimethyl diazomethylphosphonate

N⁶-benzoyl-2',3'-isopropylidene-5'-(2-hydroxytetrahydrofuran-3-yl)-5'-deoxyadenosine

Downstream raw materials:

N⁶-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

2',3'-isopropylidene-5'-(5-iodo-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

5'-(6-amino-6-carboxy-1-phenyl-1-hexyn-3-yl)-5'-deoxyadenosine

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