N²-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine

Base Information

• Chemical Name: N²-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine
• CAS No.: 832748-21-7
• Molecular Formula: C₄₅H₆₁N₉O₇Si₂
• Molecular Weight: 896.206
• Mol file: 832748-21-7.mol

Synonyms:N²-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine

Chemical Property of N²-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine

There total 5 articles about N²-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-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: 76.0%

N2-(2-amino-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine (832748-20-6) + (4-tert-butylphenoxy)acetyl chloride (90734-55-7) → N2-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine (832748-21-7)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/ol047851m

Reference yield:

5-bromo-3-methyl-2-nitro-3H-imidazo[4,5-f]quinoline (832748-17-1) → N2-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine (832748-21-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / CsCO₃; BINAP / Pd(OAc)2 / toluene / 90 °C

2: 80 percent / H₂ / Pd/C / methanol; tetrahydrofuran / 1 h / 20 °C / 760 Torr

3: 76 percent / pyridine / 20 °C

With pyridine; hydrogen; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; toluene; 1: Buchwald-Hartwig cross-coupling reaction;

DOI:10.1021/ol047851m

Reference yield:

2-amino-5-bromo-3-methyl-3H-imidazo[4,5-f]quinoline (98203-07-7) → N2-[2-(2-(4-tert-butylphenoxyacetylamino)-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)]-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine (832748-21-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / NaNO₂ / acetic acid; H₂O / 4 h / 20 °C

2: 72 percent / CsCO₃; BINAP / Pd(OAc)2 / toluene / 90 °C

3: 80 percent / H₂ / Pd/C / methanol; tetrahydrofuran / 1 h / 20 °C / 760 Torr

4: 76 percent / pyridine / 20 °C

With pyridine; hydrogen; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium nitrite; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetic acid; toluene; 2: Buchwald-Hartwig cross-coupling reaction;

DOI:10.1021/ol047851m

upstream raw materials:

N²-(2-amino-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)]-2'-deoxyguanosine

(4-tert-butylphenoxy)acetyl chloride

2-amino-5-bromo-3-methyl-3H-imidazo[4,5-f]quinoline

5-bromo-3-methyl-2-nitro-3H-imidazo[4,5-f]quinoline

Refernces