{5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester

Base Information

• Chemical Name: {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester
• CAS No.: 263758-82-3
• Molecular Formula: C₅₇H₆₅N₇O₁₆P₂S
• Molecular Weight: 1198.19

Synonyms:

Chemical Property of {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester

There total 15 articles about {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester 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:

2'-deoxy-5-(hydroxymethyl)uridine (5116-24-5,15425-01-1,143156-50-7) → {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester (263758-82-3)

Guidance literature:

Multi-step reaction with 13 steps

1: chlorotrimethylsilane / dioxane / 2.5 h / 50 °C

2: NaN₃ / dimethylformamide / 0.25 h / 60 °C

3: 70 percent / pyridine / 1.5 h / 20 °C

4: CF₃COOH / CH₂Cl₂ / 10 h

5: H₂ / Pd/C / methanol / 14 h

6: Et₃N / dimethylformamide / 1 h

7: 71 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h

8: 76 percent / isodurenedisulfonyl dichloride; 1H-tetrazole; pyridine / 1 h

9: KOH; water / pyridine / 3 h

10: isodurenedisulfonyl dichloride; pyridine; 1H-tetrazole / 0.33 h

11: AcOH; water / 5 h

12: pyridine / 20 h

13: 71 percent / iPr₂EtN / CH₂Cl₂ / 1 h

With pyridine; 1H-tetrazole; potassium hydroxide; chloro-trimethyl-silane; sodium azide; tetrabutyl ammonium fluoride; water; hydrogen; acetic acid; 2,4,5,6-tetramethylbenzenedisulfonyl dichloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution / 3: Acylation / 4: Etherification / 5: Hydrogenation / 6: Condensation / 7: deprotection / 8: Condensation / 9: Hydrolysis / 10: Cyclization / 11: Hydrolysis / 12: Etherification / 13: phosphorylation;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<162::AID-HLCA162>3.0.CO;2-Y

Reference yield:

5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (59090-48-1) → {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester (263758-82-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 70 percent / pyridine / 1.5 h / 20 °C

2: CF₃COOH / CH₂Cl₂ / 10 h

3: H₂ / Pd/C / methanol / 14 h

4: Et₃N / dimethylformamide / 1 h

5: 71 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h

6: 76 percent / isodurenedisulfonyl dichloride; 1H-tetrazole; pyridine / 1 h

7: KOH; water / pyridine / 3 h

8: isodurenedisulfonyl dichloride; pyridine; 1H-tetrazole / 0.33 h

9: AcOH; water / 5 h

10: pyridine / 20 h

11: 71 percent / iPr₂EtN / CH₂Cl₂ / 1 h

With pyridine; 1H-tetrazole; potassium hydroxide; tetrabutyl ammonium fluoride; water; hydrogen; acetic acid; 2,4,5,6-tetramethylbenzenedisulfonyl dichloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Etherification / 3: Hydrogenation / 4: Condensation / 5: deprotection / 6: Condensation / 7: Hydrolysis / 8: Cyclization / 9: Hydrolysis / 10: Etherification / 11: phosphorylation;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<162::AID-HLCA162>3.0.CO;2-Y

Reference yield:

5-Chloromethyl-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione → {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxyuridine 3'-(2-cyanoethyl diisopropylphosphoramidite) S-phenyl ester (263758-82-3)

Guidance literature:

Multi-step reaction with 12 steps

1: NaN₃ / dimethylformamide / 0.25 h / 60 °C

2: 70 percent / pyridine / 1.5 h / 20 °C

3: CF₃COOH / CH₂Cl₂ / 10 h

4: H₂ / Pd/C / methanol / 14 h

5: Et₃N / dimethylformamide / 1 h

6: 71 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h

7: 76 percent / isodurenedisulfonyl dichloride; 1H-tetrazole; pyridine / 1 h

8: KOH; water / pyridine / 3 h

9: isodurenedisulfonyl dichloride; pyridine; 1H-tetrazole / 0.33 h

10: AcOH; water / 5 h

11: pyridine / 20 h

12: 71 percent / iPr₂EtN / CH₂Cl₂ / 1 h

With pyridine; 1H-tetrazole; potassium hydroxide; sodium azide; tetrabutyl ammonium fluoride; water; hydrogen; acetic acid; 2,4,5,6-tetramethylbenzenedisulfonyl dichloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Acylation / 3: Etherification / 4: Hydrogenation / 5: Condensation / 6: deprotection / 7: Condensation / 8: Hydrolysis / 9: Cyclization / 10: Hydrolysis / 11: Etherification / 12: phosphorylation;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<162::AID-HLCA162>3.0.CO;2-Y

upstream raw materials:

4,4'-dimethoxytrityl chloride

2'-deoxy-5-(hydroxymethyl)uridine

[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-acetic acid

5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

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