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

Base Information

• Chemical Name: 3'-O-<4''-((N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethyl>-5'-O-(tert-butyldiphenylsilyl)thymidine
• CAS No.: 221303-13-5
• Molecular Formula: C₄₃H₅₄N₄O₁₁Si
• Molecular Weight: 831.007
• Mol file: 221303-13-5.mol

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

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

There total 6 articles about 3'-O-<4''-((N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethyl>-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: 49.0%

5'-O-tert-butyldiphenylsilylthymidine (101527-40-6) + 1-<(N-allyloxycarbonyl)-5'-aminopent-1-yl-oxy>-4-bromomethyl-2-methoxy-5-nitrobenzene (221895-90-5) → 3'-O-<4''-((N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethyl>-5'-O-(tert-butyldiphenylsilyl)thymidine (221303-13-5)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydroxide; water; sodium iodide; In chloroform; at 25 ℃; for 16h;

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-allyloxycarbonyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethyl>-5'-O-(tert-butyldiphenylsilyl)thymidine (221303-13-5)

Guidance literature:

Multi-step reaction with 5 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: 88 percent / CBr₄, PPh₃ / ethyl acetate / 1 h / 25 °C

5: 49 percent / Bu₄NOH, NaI, NaOH, H₂₀ / CHCl₃ / 16 h / 25 °C

With sodium hydroxide; sodium tetrahydroborate; carbon tetrabromide; tetra(n-butyl)ammonium hydroxide; water; nitric acid; acetic anhydride; potassium carbonate; triphenylphosphine; potassium iodide; sodium iodide; In ethanol; chloroform; ethyl acetate; 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-allyloxycarbonyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethyl>-5'-O-(tert-butyldiphenylsilyl)thymidine (221303-13-5)

Guidance literature:

Multi-step reaction with 5 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: 88 percent / CBr₄, PPh₃ / ethyl acetate / 1 h / 25 °C

5: 49 percent / Bu₄NOH, NaI, NaOH, H₂₀ / CHCl₃ / 16 h / 25 °C

With sodium hydroxide; sodium tetrahydroborate; carbon tetrabromide; tetra(n-butyl)ammonium hydroxide; water; nitric acid; acetic anhydride; potassium carbonate; triphenylphosphine; potassium iodide; sodium iodide; In ethanol; chloroform; ethyl acetate; acetonitrile;

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

upstream raw materials:

5'-O-tert-butyldiphenylsilylthymidine

1-<(N-allyloxycarbonyl)-5'-aminopent-1-yl-oxy>-4-bromomethyl-2-methoxy-5-nitrobenzene

vanillin

allyl (5-bromopentyl)carbamate

Downstream raw materials:

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

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