{5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine 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'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine S-phenyl ester
• CAS No.: 263758-81-2
• Molecular Formula: C₅₃H₅₆N₅O₁₆PS
• Molecular Weight: 1082.09

Synonyms:

Chemical Property of {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine 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'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine S-phenyl ester

There total 13 articles about {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine 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:

3,4-dihydro-2H-pyran (110-87-2) → {5:2'-O-[methyleneimino(2-oxoethane-2,1-diyl)]}-linked 5'-O-(4,4'-dimethoxytrityl)-P-thiouridyl-(3'->5')-2'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine S-phenyl ester (263758-81-2)

Guidance literature:

Multi-step reaction with 7 steps

1: CF₃COOH / CH₂Cl₂ / 10 h

2: H₂ / Pd/C / methanol / 14 h

3: Et₃N / dimethylformamide / 1 h

4: 71 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h

5: 76 percent / isodurenedisulfonyl dichloride; 1H-tetrazole; pyridine / 1 h

6: KOH; water / pyridine / 3 h

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

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

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

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'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine S-phenyl ester (263758-81-2)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; 1H-tetrazole; potassium hydroxide; chloro-trimethyl-silane; sodium azide; tetrabutyl ammonium fluoride; water; hydrogen; 2,4,5,6-tetramethylbenzenedisulfonyl dichloride; triethylamine; 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;

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'-deoxy-3'-O-(tetrahdyro-2H-pyran-2-yl)uridine S-phenyl ester (263758-81-2)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 1H-tetrazole; potassium hydroxide; tetrabutyl ammonium fluoride; water; hydrogen; 2,4,5,6-tetramethylbenzenedisulfonyl dichloride; triethylamine; 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;

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

upstream raw materials:

3,4-dihydro-2H-pyran

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

Downstream raw materials:

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

{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

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