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

Base Information

• Chemical Name: 3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine
• CAS No.: 1232359-33-9
• Molecular Formula: C₂₁H₂₆N₂O₇
• Molecular Weight: 418.447
• Mol file: 1232359-33-9.mol

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

Chemical Property of 3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of 3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine

There total 1 articles about 3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine 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: 93.0%

2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine (1204744-83-1) → 3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine (1232359-33-9)

Guidance literature:

2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine; With methanol; potassium carbonate; for 4h;

With acetic acid; In methanol; for 0.0833333h;

DOI:10.1134/S1068162010020093

Reference yield: 97.0%

3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine (1232359-33-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 3'-O-benzyl-2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine (1232359-36-2)

Guidance literature:

With 1H-imidazole; In acetonitrile;

DOI:10.1134/S1068162010020093

Reference yield:

3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine (1232359-33-9) → 2'-O-tert-butyldimethylsilyl-5'-deoxy-5'-{[N-(5'-O-(4,4'-dimethoxytrityl)-3'-deoxythymidine-3'-yl)carboxamido]methyl}ribosylthymine (1232359-53-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1H-imidazole / acetonitrile

2: potassium hydroxide / ethanol / 1 h

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

4: trifluoroacetic acid / water / 0.33 h / 0 °C

5: palladium 10% on activated carbon; hydrogen / 5 h / 20 °C / 760.05 Torr

6: pyridine

With pyridine; 1H-imidazole; palladium 10% on activated carbon; hydrogen; 1,1'-carbonyldiimidazole; trifluoroacetic acid; potassium hydroxide; In ethanol; dichloromethane; water; acetonitrile;

DOI:10.1134/S1068162010020093

upstream raw materials:

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

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'-carboxymethylribosylthymine

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