N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine
• CAS No.: 878550-05-1
• Molecular Formula: C₄₄H₄₉N₅O₄Si
• Molecular Weight: 739.99

Synonyms:N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine

Chemical Property of N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine

Chemical Property:

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Technology Process of N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine

There total 12 articles about N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine 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: 84.0%

N6-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-hydroxycyclohexyl}adenine (878550-03-9) + mono-4-methoxytrityl chloride (14470-28-1) → N6-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine (878550-05-1)

Guidance literature:

With pyridine;

DOI:10.1002/hlca.200590258

Reference yield:

(+/-)-5-amino-4-[(1'RS,2'RS,4'RS)-4'-(benzyloxy)-2'-hydroxycyclohexylamine]-6-chloropyrimidine → N6-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine (878550-05-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: HCl / 20 °C

1.2: 76 percent / HCl / tetrahydrofuran / 2 h / 20 °C

2.1: 84 percent / NH₃ / methanol / 100 °C

3.1: 81 percent / 1H-imidazole / dimethylformamide / 20 °C

4.1: 96 percent / NH₄OCOH / Pd/C / methanol / 7 h / Heating

5.1: pyridine / 1 h / 0 °C

6.1: pyridine / 20 °C

7.1: 521 mg / NH₄OH / H₂O; methanol / 0.5 h / 0 °C

8.1: 36 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

9.1: 66 percent / NaOH / methanol; dioxane

10.1: 84 percent / pyridine

With pyridine; 1H-imidazole; hydrogenchloride; dmap; ammonium hydroxide; sodium hydroxide; ammonia; ammonium formate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200590258

Reference yield:

(+/-)-9-[(1'RS,2'RS,4'RS)-4'-(benzyloxy)-2'-hydroxycyclohexyl]-6-chloropurine → N6-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine (878550-05-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / NH₃ / methanol / 100 °C

2: 81 percent / 1H-imidazole / dimethylformamide / 20 °C

3: 96 percent / NH₄OCOH / Pd/C / methanol / 7 h / Heating

4: pyridine / 1 h / 0 °C

5: pyridine / 20 °C

6: 521 mg / NH₄OH / H₂O; methanol / 0.5 h / 0 °C

7: 36 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

8: 66 percent / NaOH / methanol; dioxane

9: 84 percent / pyridine

With pyridine; 1H-imidazole; dmap; ammonium hydroxide; sodium hydroxide; ammonia; ammonium formate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200590258

upstream raw materials:

N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-hydroxycyclohexyl}adenine

mono-4-methoxytrityl chloride

N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(R)-2-methoxy-2-phenylacetoxy]cyclohexyl}adenine

(+/-)-(1RS,2RS,5RS)-2-amino-5-(benzyloxy)cyclohexan-1-ol

Downstream raw materials:

Diisopropyl-phosphoramidous acid (1S,2S,5S)-2-(6-benzoylamino-purin-9-yl)-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-cyclohexyl ester 2-cyano-ethyl ester

N⁶-benzoyl-9-{2'-hydroxy-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine

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