(2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol

Base Information

• Chemical Name: (2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol
• CAS No.: 1072091-12-3
• Molecular Formula: C₂₂H₂₉NO₃
• Molecular Weight: 355.477
• Mol file: 1072091-12-3.mol

Synonyms:(2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol

Chemical Property of (2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol

There total 6 articles about (2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol 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:

N-[(1S,2E)-4-(benzyloxy)-1-((1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-methylbut-2-en-1-yl]-4-methoxyaniline (1072091-09-8) → (2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol (1072091-12-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield:

ethyl (4-methoxyphenylimino)acetate (124156-21-4) → (2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol (1072091-12-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid / dimethyl sulfoxide / 1 h / 20 °C

2.1: sodium tetrahydroborate / methanol; dimethyl sulfoxide / 0.5 h / 0 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 10.5 h / 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -10 °C

5.1: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

6.1: toluene / 36 h / Heating / reflux

6.2: 1 h / 0 °C

7.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C

7.2: 1 h / 0 °C

8.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

8.2: 19 h / 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; lithium hexamethyldisilazane; (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

Reference yield:

ethyl (2S,3R)-3-formyl-2-(4-methoxyphenylamino)butanoate (409095-87-0) → (2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol (1072091-12-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium tetrahydroborate / methanol; dimethyl sulfoxide / 0.5 h / 0 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 10.5 h / 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -10 °C

4.1: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

5.1: toluene / 36 h / Heating / reflux

5.2: 1 h / 0 °C

6.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C

6.2: 1 h / 0 °C

7.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

7.2: 19 h / 20 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

upstream raw materials:

N-[(1S,2E)-4-(benzyloxy)-1-((1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-methylbut-2-en-1-yl]-4-methoxyaniline

ethyl (2S,3R)-3-formyl-2-(4-methoxyphenylamino)butanoate

ethyl (2E,4S,5R)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-[(4-methoxyphenyl)amino]-3,5-dimethylhex-2-enoate

ethyl (2S,3R)-4-hydroxy-2-[(4-methoxyphenyl)amino]-3-methylbutanoate

Downstream raw materials:

tert-butyl {(1S,2E)-4-(benzyloxy)-1-[(1R)-2-hydroxy-1-methylethyl]-2-methylbut-2-en-1-yl}carbamate

N-{(1S,2E)-4-(benzyloxy)-1-[(1S,2E)-3-iodo-1-methylprop-2-en-1-yl]-2-methylbut-2-en-1-yl}-7-hydroxyheptaneamide

C₁₆H₂₂INO

C₁₇H₂₄INO