3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine

Base Information

• Chemical Name: 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine
• CAS No.: 221896-04-4
• Molecular Formula: C₅₂H₆₁N₅O₁₃SSi
• Molecular Weight: 1024.23
• Mol file: 221896-04-4.mol

Synonyms:3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine

Chemical Property of 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine

There total 8 articles about 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine 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:

vanillin (121-33-5,8014-42-4) → 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine (221896-04-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / K₂CO₃, KI / acetonitrile / 12 h / Heating

2: Ac₂O, HNO₃ / 1.) 0 deg C, 2 h, 2.) 25 deg C, 2 h

3: NaBH₄ / ethanol / 4 h / 0 °C

4: tetrahydrofuran; toluene / 1.5 h / 25 °C

5: 1.) NaH / 1.) THF, 25 deg C, 1 h, 2.) THF, 0 deg C, 30 min; 25 deg C, 1.5 h

6: HNEt₂ / Pd(PPh₃)4 / tetrahydrofuran / 2.5 h / 25 °C

7: NEt₃, DMAP / toluene; tetrahydrofuran / 1.) 25 deg C, 15 min, 2.) 25 deg C, 1 h

With dmap; sodium tetrahydroborate; nitric acid; acetic anhydride; sodium hydride; potassium carbonate; diethylamine; triethylamine; potassium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; toluene; acetonitrile;

DOI:10.1002/(SICI)1521-3765(19990301)5:3<951::AID-CHEM951>3.0.CO;2-G

Reference yield:

[5-(4-formyl-2-methoxy-5-nitro-phenoxy)-pentyl]-carbamic acid allyl ester → 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine (221896-04-4)

Guidance literature:

Multi-step reaction with 5 steps

1: NaBH₄ / ethanol / 4 h / 0 °C

2: tetrahydrofuran; toluene / 1.5 h / 25 °C

3: 1.) NaH / 1.) THF, 25 deg C, 1 h, 2.) THF, 0 deg C, 30 min; 25 deg C, 1.5 h

4: HNEt₂ / Pd(PPh₃)4 / tetrahydrofuran / 2.5 h / 25 °C

5: NEt₃, DMAP / toluene; tetrahydrofuran / 1.) 25 deg C, 15 min, 2.) 25 deg C, 1 h

With dmap; sodium tetrahydroborate; sodium hydride; diethylamine; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; toluene;

DOI:10.1002/(SICI)1521-3765(19990301)5:3<951::AID-CHEM951>3.0.CO;2-G

Reference yield:

allyl (5-bromopentyl)carbamate (221303-08-8) → 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-5'-O-(tert-butyldiphenylsilyl)thymidine (221896-04-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / K₂CO₃, KI / acetonitrile / 12 h / Heating

2: Ac₂O, HNO₃ / 1.) 0 deg C, 2 h, 2.) 25 deg C, 2 h

3: NaBH₄ / ethanol / 4 h / 0 °C

4: tetrahydrofuran; toluene / 1.5 h / 25 °C

5: 1.) NaH / 1.) THF, 25 deg C, 1 h, 2.) THF, 0 deg C, 30 min; 25 deg C, 1.5 h

6: HNEt₂ / Pd(PPh₃)4 / tetrahydrofuran / 2.5 h / 25 °C

7: NEt₃, DMAP / toluene; tetrahydrofuran / 1.) 25 deg C, 15 min, 2.) 25 deg C, 1 h

With dmap; sodium tetrahydroborate; nitric acid; acetic anhydride; sodium hydride; potassium carbonate; diethylamine; triethylamine; potassium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; toluene; acetonitrile;

DOI:10.1002/(SICI)1521-3765(19990301)5:3<951::AID-CHEM951>3.0.CO;2-G

upstream raw materials:

5-(dimethylamino)naphth-1-ylsulfonyl chloride

vanillin

allyl (5-bromopentyl)carbamate

4-<(N-allyloxycarbonyl)-5-aminopent-1-yl-oxy>-3-methoxybenzaldehyde

Downstream raw materials:

3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>thymidine