5'-O-(4,4'-dimethoxytrityl)-N²-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-N²-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine
• CAS No.: 253586-23-1
• Molecular Formula: C₄₃H₅₅N₅O₉Si
• Molecular Weight: 814.023
• Mol file: 253586-23-1.mol

Synonyms:5'-O-(4,4'-dimethoxytrityl)-N²-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-N²-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(4,4'-dimethoxytrityl)-N²-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine

There total 9 articles about 5'-O-(4,4'-dimethoxytrityl)-N²-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine 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: 60.0%

N2-acetyl-5'-O-(4,4'-dimethoxytrityl)guanosine (231957-27-0) + chloromethoxy-triisopropyl-silane (217300-17-9) → N2-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}guanosine (415707-14-1) + 5'-O-(4,4'-dimethoxytrityl)-N2-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine (253586-23-1)

Guidance literature:

N²-acetyl-5'-O-(4,4'-dimethoxytrityl)guanosine; With dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 25 ℃; for 1h;

chloromethoxy-triisopropyl-silane; In 1,2-dichloro-ethane; at 70 ℃; for 0.5h;

DOI:10.1002/(SICI)1522-2675(19991006)82:10<1753::AID-HLCA1753>3.0.CO;2-Y

Reference yield:

triisopropylsilyl (ethylthio)methyl ether (253586-28-6) → 5'-O-(4,4'-dimethoxytrityl)-N2-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine (253586-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / SO₂Cl₂ / CH₂Cl₂ / 1 h / 4 - 20 °C

2.1: iPr₂NEt; Bu₂SnCl₂ / 1,2-dichloro-ethane / 1 h / 20 °C

2.2: 60 percent / CH₂Cl₂ / 0.33 h / 80 °C

With sulfuryl dichloride; dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/1522-2675(20011219)84:12<3773::AID-HLCA3773>3.0.CO;2-E

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (30747-23-0) → 5'-O-(4,4'-dimethoxytrityl)-N2-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine (253586-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 50.5 g / NaOH; H₂O / tetrahydrofuran; methanol / 0.33 h / 20 °C

2.1: 81 percent / pyridine / dimethylformamide / 1 h / 20 °C

3.1: iPr₂NEt; Bu₂SnCl₂ / 1,2-dichloro-ethane / 1 h / 20 °C

3.2: 60 percent / CH₂Cl₂ / 0.33 h / 80 °C

With pyridine; sodium hydroxide; dibutyltin chloride; water; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(20011219)84:12<3773::AID-HLCA3773>3.0.CO;2-E

upstream raw materials:

N²-acetyl-5'-O-(4,4'-dimethoxytrityl)guanosine

chloromethoxy-triisopropyl-silane

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

N²-acetylguanosine