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

Base Information

• Chemical Name: 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine
• CAS No.: 479408-36-1
• Molecular Formula: C₅₅H₇₀N₆O₇Si₂
• Molecular Weight: 983.368
• Mol file: 479408-36-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-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: 97.0%

2-(4-isopropylphenoxy)acetyl chloride (223128-33-4) + 8-(N-acetyl-2-amino-fluorene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-35-0) → 8-(N-acetyl-2-amino-fluorene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N2-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine (479408-36-1)

Guidance literature:

In pyridine; at 20 ℃;

DOI:10.1021/ol026474f

Reference yield:

8-bromo-2'-deoxyguanosine (13389-03-2) → 8-(N-acetyl-2-amino-fluorene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N2-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine (479408-36-1)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 1H-imidazole; hydrogenchloride; dmap; di-isopropyl azodicarboxylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 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:

tert-butyldimethylsilyl chloride (18162-48-6) → 8-(N-acetyl-2-amino-fluorene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N2-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine (479408-36-1)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 1H-imidazole; hydrogenchloride; dmap; di-isopropyl azodicarboxylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 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

upstream raw materials:

acetic anhydride

N-[6-benzyloxy-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(9H-fluoren-2-ylamino)-9H-purin-2-yl]-2-(4-isopropyl-phenoxy)-acetamide

2-(4-isopropylphenoxy)acetyl chloride

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

Downstream raw materials:

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

2-fluoren

fluorene

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