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)

Base Information

Chemical Name: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)
CAS No.:1232359-54-4
Molecular Formula:C₅₈H₇₈N₇O₁₃PSi
Molecular Weight:1140.36
Hs Code.:

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)

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Chemical Property of 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)

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Technology Process of 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)

There total 12 articles about 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) 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: 74.0%

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

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 1232359-54-4
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)

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 2h;
DOI:10.1134/S1068162010020093

Reference yield:

: 1204744-83-1
2'-O-acetyl-3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethyl-5-methyluridine

: 1232359-54-4
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)

Guidance literature:: Multi-step reaction with 8 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

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h

With pyridine; 1H-imidazole; methanol; palladium 10% on activated carbon; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; potassium hydroxide; In ethanol; dichloromethane; water; acetonitrile;
DOI:10.1134/S1068162010020093

Reference yield:

: 1232359-33-9
3'-O-benzyl-5'-deoxy-5'-ethoxycarbonylmethylribosylthymine

: 1232359-54-4
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)

Guidance literature:: Multi-step reaction with 7 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

7: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h

With pyridine; 1H-imidazole; palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; potassium hydroxide; In ethanol; dichloromethane; water; acetonitrile;
DOI:10.1134/S1068162010020093