1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene

Base Information

• Chemical Name: 1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene
• CAS No.: 852310-63-5
• Molecular Formula: C₂₀H₂₃N₃O₃
• Molecular Weight: 353.421
• Mol file: 852310-63-5.mol

Synonyms:1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene

Chemical Property of 1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene

There total 8 articles about 1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene 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:

Methanesulfonic acid (E)-(1S,2S)-2-(4-methoxy-benzyloxy)-4-(4-methoxy-phenyl)-1-methyl-but-3-enyl ester (906478-67-9) → 1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene (852310-63-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/j.tetlet.2005.02.140

Reference yield:

4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol (852310-60-2) → 1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene (852310-63-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaIO₄ / methanol; H₂O / 4 h / 0 - 20 °C

2.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C

2.2: 2.94 g / tetrahydrofuran / -78 - 20 °C

3.1: 97 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

4.1: 2.8 g / triethylamine / CH₂Cl₂ / 2 h / 20 °C

5.1: 1.5 g / NaN₃ / dimethylformamide / 6 h / 70 °C

With sodium tetrahydroborate; sodium periodate; sodium azide; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2006.05.007

Reference yield:

2-(4-methoxybenzyloxy)-4-(4-methoxyphenyl)-1-methyl-(1S,2S,3E)-3-butenyl formate (852310-57-7) → 1-[4-azido-3-(4-methoxybenzyloxy)-(E,3S,4R)-1-pentenyl]-4-methoxybenzene (852310-63-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

2: 2.8 g / triethylamine / CH₂Cl₂ / 2 h / 20 °C

3: 1.5 g / NaN₃ / dimethylformamide / 6 h / 70 °C

With sodium tetrahydroborate; sodium azide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2006.05.007

upstream raw materials:

Methanesulfonic acid (E)-(1S,2S)-2-(4-methoxy-benzyloxy)-4-(4-methoxy-phenyl)-1-methyl-but-3-enyl ester

4-(4-methoxybenzyloxy)-5-methyl-(3S,4R,5S)-tetrahydro-2,3-furandiol

6-(4-methoxybenzyloxy)-2,2,5-trimethyl-(3aS,5S,6R,6aS)-perhydrofurol[2,3-d][1,3]dioxole

2-(4-methoxybenzyloxy)-4-(4-methoxyphenyl)-1-methyl-(1S,2S,3E)-3-butenyl formate

Downstream raw materials:

4-azido-1-(4-methoxyphenyl)-(E,3S,4R)-1-penten-3-ol

2-[tert-butoxycarbonylamino]-(2R,3S,4E)-5-(4-methoxyphenyl)-pent-4-en-3-ol

(E)-(3S,4R)-4-Amino-1-(4-methoxy-phenyl)-pent-1-en-3-ol