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

Base Information

• Chemical Name: 4-<(N-allyloxycarbonyl)-5-aminopent-1-yl-oxy>-3-methoxybenzaldehyde
• CAS No.: 221303-09-9
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 221303-09-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 4-<(N-allyloxycarbonyl)-5-aminopent-1-yl-oxy>-3-methoxybenzaldehyde 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: 100.0%

vanillin (121-33-5,8014-42-4) + allyl (5-bromopentyl)carbamate (221303-08-8) → 4-<(N-allyloxycarbonyl)-5-aminopent-1-yl-oxy>-3-methoxybenzaldehyde (221303-09-9)

Guidance literature:

With potassium carbonate; potassium iodide; In acetonitrile; for 12h; Heating;

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

Reference yield:

4-<(N-allyloxycarbonyl)-5-aminopent-1-yl-oxy>-3-methoxybenzaldehyde (221303-09-9) → 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethyl>thymidine (221303-14-6)

Guidance literature:

Multi-step reaction with 7 steps

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

2: NaBH₄ / ethanol / 4 h / 0 °C

3: 88 percent / CBr₄, PPh₃ / ethyl acetate / 1 h / 25 °C

4: 49 percent / Bu₄NOH, NaI, NaOH, H₂₀ / CHCl₃ / 16 h / 25 °C

5: HNEt₂ / Pd(PPh₃)4 / tetrahydrofuran / 1.25 h / 25 °C

6: NEt₃, DMAP / tetrahydrofuran; dimethylformamide / 6 h / 25 °C

7: 92 percent / TBAF / tetrahydrofuran / 0.75 h / 25 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; carbon tetrabromide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; nitric acid; acetic anhydride; diethylamine; triethylamine; triphenylphosphine; sodium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; chloroform; ethyl acetate; N,N-dimethyl-formamide;

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

Reference yield:

4-<(N-allyloxycarbonyl)-5-aminopent-1-yl-oxy>-3-methoxybenzaldehyde (221303-09-9) → 3'-O-<4''-((N-dansyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethyl>thymidine 5'-O-triphosphate

Guidance literature:

Multi-step reaction with 8 steps

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

2: NaBH₄ / ethanol / 4 h / 0 °C

3: 88 percent / CBr₄, PPh₃ / ethyl acetate / 1 h / 25 °C

4: 49 percent / Bu₄NOH, NaI, NaOH, H₂₀ / CHCl₃ / 16 h / 25 °C

5: HNEt₂ / Pd(PPh₃)4 / tetrahydrofuran / 1.25 h / 25 °C

6: NEt₃, DMAP / tetrahydrofuran; dimethylformamide / 6 h / 25 °C

7: 92 percent / TBAF / tetrahydrofuran / 0.75 h / 25 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; carbon tetrabromide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; nitric acid; acetic anhydride; diethylamine; triethylamine; triphenylphosphine; sodium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; chloroform; ethyl acetate; N,N-dimethyl-formamide;

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

upstream raw materials:

vanillin

allyl (5-bromopentyl)carbamate

Downstream raw materials:

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

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

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

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