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

Base Information

• Chemical Name: N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(R)-2-methoxy-2-phenylacetoxy]cyclohexyl}adenine
• CAS No.: 878550-01-7
• Molecular Formula: C₃₃H₄₁N₅O₅Si
• Molecular Weight: 615.805

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

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

Chemical Property:

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

There total 10 articles about N⁶-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(R)-2-methoxy-2-phenylacetoxy]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: 36.0%

(+/-)-N6-benzoyl-9-{(1'RS,2'RS,4'RS)-2'-[(tert-butyl)dimethylsilyloxy]-4'-hydroxycyclohexyl}adenine + (R)-methoxyphenylacetic acid (3966-32-3) → N6-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(R)-2-methoxy-2-phenylacetoxy]cyclohexyl}adenine (878549-91-8) + N6-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(R)-2-methoxy-2-phenylacetoxy]cyclohexyl}adenine (878550-01-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 3h;

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'-[(R)-2-methoxy-2-phenylacetoxy]cyclohexyl}adenine (878550-01-7)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; dmap; ammonium hydroxide; ammonia; ammonium formate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 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]adenine → N6-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(R)-2-methoxy-2-phenylacetoxy]cyclohexyl}adenine (878550-01-7)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 96 percent / NH₄OCOH / Pd/C / methanol / 7 h / Heating

3: pyridine / 1 h / 0 °C

4: pyridine / 20 °C

5: 521 mg / NH₄OH / H₂O; methanol / 0.5 h / 0 °C

6: 36 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

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

DOI:10.1002/hlca.200590258

upstream raw materials:

(R)-methoxyphenylacetic acid

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

(+/-)-(1RS,2RS,5RS)-2-azido-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'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine

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

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

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