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

Base Information

• Chemical Name: 2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine
• CAS No.: 1204744-83-1
• Molecular Formula: C₂₃H₂₈N₂O₈
• Molecular Weight: 460.484
• Mol file: 1204744-83-1.mol

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

Chemical Property of 2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine

There total 1 articles about 2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine 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: 95.6%

3-O-benzyl-5-deoxy-1,2-di-O-acetyl-5-ethoxycarbonylmethyl-D-ribofuranose (1204744-82-0) + thymin (65-71-4,28806-14-6,691841-57-3) → 2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine (1204744-83-1)

Guidance literature:

3-O-benzyl-5-deoxy-1,2-di-O-acetyl-5-ethoxycarbonylmethyl-D-ribofuranose; thymin; With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 4h; Reflux;

With water; sodium hydrogencarbonate; for 0.5h;

DOI:10.1134/S1068162009050082

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:

2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine (1204744-83-1) → 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 7 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

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

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

7.1: pyridine

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

DOI:10.1134/S1068162010020093

upstream raw materials:

3-O-benzyl-5-deoxy-1,2-di-O-acetyl-5-ethoxycarbonylmethyl-D-ribofuranose

thymin

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-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine

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