8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine

Base Information

• Chemical Name: 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine
• CAS No.: 479408-42-9
• Molecular Formula: C₄₃H₄₂N₆O₇
• Molecular Weight: 754.842

Synonyms:8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine

Chemical Property of 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine

There total 13 articles about 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine 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: 79.0%

8-(N-acetyl-2-amino-fluorene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N2-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine (479408-36-1) → 8-(N-acetyl-2-amino-fluorene)-O6-benzyl-N2-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine (479408-42-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol026474f

Reference yield:

8-bromo-2'-deoxyguanosine (13389-03-2) → 8-(N-acetyl-2-amino-fluorene)-O6-benzyl-N2-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine (479408-42-9)

Guidance literature:

Multi-step reaction with 8 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: 72 percent / sodium tert-butoxide; rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / tris(dibenzylideneaceton)-dipalladium / toluene / 1 h / 100 °C

5: triethylamine; 4-(dimethylamino)pyridine / pyridine / 5 h / 20 °C

6: 78 percent / hydrochloric acid / methanol / 20 °C

7: 97 percent / pyridine / 20 °C

8: 79 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 20 °C

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

DOI:10.1021/ol026474f

Reference yield:

O6-benzyl-8-bromo-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-22-5) → 8-(N-acetyl-2-amino-fluorene)-O6-benzyl-N2-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine (479408-42-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / pyridine / 20 °C

2: 72 percent / sodium tert-butoxide; rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / tris(dibenzylideneaceton)-dipalladium / toluene / 1 h / 100 °C

3: triethylamine; 4-(dimethylamino)pyridine / pyridine / 5 h / 20 °C

4: 78 percent / hydrochloric acid / methanol / 20 °C

5: 97 percent / pyridine / 20 °C

6: 79 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 20 °C

With pyridine; hydrogenchloride; dmap; tetrabutyl ammonium fluoride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; acetic acid; triethylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; pyridine; methanol; toluene; 2: Buchwald-Hartwig coupling;

DOI:10.1021/ol026474f

upstream raw materials:

8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine

2-aminofluorene

2-(4-isopropylphenoxy)acetic acid

8-bromo-2'-deoxyguanosine

Downstream raw materials:

8-(N-acetyl-2-amino-fluorene)-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine

2-fluoren

fluorene

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