3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine

Base Information

• Chemical Name: 3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine
• CAS No.: 1232359-45-3
• Molecular Formula: C₄₁H₆₃N₅O₁₀Si₂
• Molecular Weight: 842.15
• Mol file: 1232359-45-3.mol

Synonyms:3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine

Chemical Property of 3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine

There total 7 articles about 3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine 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: 81.0%

3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-carboxymethylribosylthymine (1232359-39-5) + 1-((2R,4S,5S)-4-amino-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (130945-04-9) → 3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine (1232359-45-3)

Guidance literature:

3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-carboxymethylribosylthymine; With 1,1'-carbonyldiimidazole; In dichloromethane; for 1h;

1-((2R,4S,5S)-4-amino-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione; In dichloromethane;

DOI:10.1134/S1068162010020093

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine (1232359-45-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / acetonitrile

2: potassium hydroxide / ethanol / 1 h

3: 1,1'-carbonyldiimidazole / dichloromethane / 1 h

With 1H-imidazole; 1,1'-carbonyldiimidazole; potassium hydroxide; In ethanol; dichloromethane; acetonitrile;

DOI:10.1134/S1068162010020093

Reference yield:

2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine (1204744-83-1) → 3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine (1232359-45-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methanol; potassium carbonate / 4 h

1.2: 0.08 h

2.1: 1H-imidazole / acetonitrile

3.1: potassium hydroxide / ethanol / 1 h

4.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h

With 1H-imidazole; methanol; potassium carbonate; 1,1'-carbonyldiimidazole; potassium hydroxide; In ethanol; dichloromethane; acetonitrile;

DOI:10.1134/S1068162010020093

upstream raw materials:

2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine

3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine

3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine

3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-carboxymethylribosylthymine

Downstream raw materials:

2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-(4,4'-dimethoxytrityl)-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine

2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-(4,4'-dimethoxytrityl)-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine-3'-(2-cyanethyl-N-diisopropylphosphoramidite)

3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'{[N-(3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine