3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N²-acetyl-2'-deoxyguanosine

Base Information

• Chemical Name: 3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N²-acetyl-2'-deoxyguanosine
• CAS No.: 439115-30-7
• Molecular Formula: C₅₀H₆₂N₇O₁₂P
• Molecular Weight: 984.056

Synonyms:3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N²-acetyl-2'-deoxyguanosine

Chemical Property of 3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N²-acetyl-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of 3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N²-acetyl-2'-deoxyguanosine

There total 8 articles about 3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N²-acetyl-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: 95.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N2-acetyl-2'-deoxyguanosine (439115-29-4) → 3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N2-acetyl-2'-deoxyguanosine (439115-30-7)

Guidance literature:

With 1H-tetrazole; In pyridine; dichloromethane; for 3h;

DOI:10.1021/tx010181y

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N2-acetyl-2'-deoxyguanosine (439115-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / pyridine / 5 h / 20 °C

2: 95 percent / 1H-tetrazole / CH₂Cl₂; pyridine / 3 h

With pyridine; 1H-tetrazole; In pyridine; dichloromethane;

DOI:10.1021/tx010181y

Reference yield:

2'-Deoxyguanosine (961-07-9) → 3'-O-[(N,N-diisopropylamino)-2-cyanoethoxyphosphinyl]-5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N2-acetyl-2'-deoxyguanosine (439115-30-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaOH / N,N-dimethyl-acetamide / 1 h / 70 °C

1.2: 65 percent / N,N-dimethyl-acetamide / 20 - 60 °C

2.1: 90 percent / 1H-imidazole / dimethylformamide

3.1: 87 percent / N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 20 °C

4.1: 84 percent / triethylamine; 4-(dimethylamino)pyridine / pyridine / 80 h / 55 °C

5.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: 73 percent / pyridine / 5 h / 20 °C

7.1: 95 percent / 1H-tetrazole / CH₂Cl₂; pyridine / 3 h

With pyridine; 1H-imidazole; 1H-tetrazole; dmap; sodium hydroxide; osmium(VIII) oxide; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;

DOI:10.1021/tx010181y

upstream raw materials:

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

5'-O-(4,4'-dimethoxytrityl)-1-(3,4-diacetoxybut-1-yl)-N²-acetyl-2'-deoxyguanosine

4,4'-dimethoxytrityl chloride

2'-Deoxyguanosine

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