N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Base Information

• Chemical Name: N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine
• CAS No.: 253586-22-0
• Molecular Formula: C₄₃H₅₅N₅O₈Si
• Molecular Weight: 798.024
• Mol file: 253586-22-0.mol

Synonyms:N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Chemical Property of N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

There total 10 articles about N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine 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: 40.0%

N6-acetyl-5'-O-(4,4'-dimethoxytrityl)adenosine (231957-26-9) + chloromethoxy-triisopropyl-silane (217300-17-9) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (253586-22-0) + N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (415707-13-0)

Guidance literature:

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)adenosine; 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) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (253586-22-0)

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: 40 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:

O2',O3',O5'-tris-trimethylsilanyl-adenosine (10457-15-5) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (253586-22-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / acetonitrile / 1 h / 4 °C

2.1: 91 g / AcOH / methanol / 48 h / -20 °C

3.1: 75 percent / pyridine / 1 h / 20 °C

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

4.2: 40 percent / CH₂Cl₂ / 0.33 h / 80 °C

With pyridine; dibutyltin chloride; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; 1,2-dichloro-ethane; acetonitrile;

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

upstream raw materials:

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)adenosine

chloromethoxy-triisopropyl-silane

O^2'_,O3'_,O5'-tris-trimethylsilanyl-adenosine

triisopropylsilyl chloride

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-N⁶-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}adenosine 3'-(2-cyanoethyl diisopropylphosphoramidite)

5'-O-(4,4'-dimethoxytrityl)-N⁶-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyloxy)methyl]adenosine}

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

(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-triisopropylsilanyloxymethoxy-tetrahydro-furan-3-ol