3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine

Base Information

• Chemical Name: 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine
• CAS No.: 221896-08-8
• Molecular Formula: C₄₃H₄₆N₈O₁₂S
• Molecular Weight: 898.951

Synonyms:3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine

Chemical Property of 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine

Chemical Property:

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Technology Process of 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine

There total 9 articles about 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine 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: 75.0%

3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-5'-O-(tert-butyldiphenylsilyl)-N-6-benzoyladenosine (221896-06-6) → 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine (221896-08-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.3h;

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

Reference yield:

vanillin (121-33-5,8014-42-4) → 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine (221896-08-8)

Guidance literature:

Multi-step reaction with 8 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, 30 min, 2.) THF, 0 deg C, 17 h

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

7: NEt₃, DMAP / toluene; tetrahydrofuran / 25 °C

8: 75 percent / TBAF / tetrahydrofuran / 0.3 h

With dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; 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:

allyl (5-bromopentyl)carbamate (221303-08-8) → 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-N-6-benzoyladenosine (221896-08-8)

Guidance literature:

Multi-step reaction with 8 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, 30 min, 2.) THF, 0 deg C, 17 h

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

7: NEt₃, DMAP / toluene; tetrahydrofuran / 25 °C

8: 75 percent / TBAF / tetrahydrofuran / 0.3 h

With dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; 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:

3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-5'-O-(tert-butyldiphenylsilyl)-N-6-benzoyladenosine

vanillin

allyl (5-bromopentyl)carbamate

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

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