6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine

Base Information

• Chemical Name: 6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine
• CAS No.: 479408-25-8
• Molecular Formula: C₆₁H₇₃N₉O₆Si₂
• Molecular Weight: 1084.48

Synonyms:6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine

Chemical Property of 6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine

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Technology Process of 6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine

There total 5 articles about 6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine 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: 68.0%

2-amino-1-methylimidazo[4,5-f]-quinoline (102408-25-3) + O6-benzyl-8-bromo-3′,5′-O-bis(tert-butyldimethylsilyl)-N2-dimethoxytrityl-2′-deoxyguanosine (479408-23-6) → 6-benzyloxy-N2-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N8-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine (479408-25-8)

Guidance literature:

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 100 ℃;

DOI:10.1021/ol026474f

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 6-benzyloxy-N2-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N8-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine (479408-25-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / imidazole / dimethylformamide; tetrahydrofuran / 5 h / 20 °C

2: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / dioxane / 5 h / 20 °C

3: 94 percent / pyridine / 20 °C

4: 68 percent / sodium tert-butoxide; rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / Pd₂(dba)3 / toluene / 100 °C

With pyridine; 1H-imidazole; di-isopropyl azodicarboxylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; 4: Buchwald-Hartwig coupling;

DOI:10.1021/ol026474f

Reference yield:

8-bromo-2'-deoxyguanosine (13389-03-2) → 6-benzyloxy-N2-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N8-(1-methyl-1H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine (479408-25-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / imidazole / dimethylformamide; tetrahydrofuran / 5 h / 20 °C

2: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / dioxane / 5 h / 20 °C

3: 94 percent / pyridine / 20 °C

4: 68 percent / sodium tert-butoxide; rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / Pd₂(dba)3 / toluene / 100 °C

With pyridine; 1H-imidazole; di-isopropyl azodicarboxylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; 4: Buchwald-Hartwig coupling;

DOI:10.1021/ol026474f

upstream raw materials:

2-amino-1-methylimidazo[4,5-f]-quinoline

O⁶-benzyl-8-bromo-3′,5′-O-bis(tert-butyldimethylsilyl)-N²-dimethoxytrityl-2′-deoxyguanosine

tert-butyldimethylsilyl chloride

8-bromo-2'-deoxyguanosine

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