(3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-ol

Base Information

• Chemical Name: (3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-ol
• CAS No.: 1313436-00-8
• Molecular Formula: C₂₃H₂₉NO
• Molecular Weight: 335.489
• Mol file: 1313436-00-8.mol

Synonyms:(3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-ol

Chemical Property of (3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-ol

There total 2 articles about (3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-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: 61.0%

Allylbenzylamine (4383-22-6) + (2S)-2-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanal (146861-20-3) + 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane (83947-56-2) → (3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-ol (1313436-00-8)

Guidance literature:

(2S)-2-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanal; With tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; for 16h; Inert atmosphere;

Allylbenzylamine; 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane; In tetrahydrofuran; ethanol; at 20 ℃; for 40h; Inert atmosphere;

DOI:10.1021/ol201349k

Reference yield:

(S)-methyl 2-(tert-butyldiphenylsilyloxy)-3-methylbutanoate (146861-09-8) → (3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-ol (1313436-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran; ethanol / 16 h / Inert atmosphere

2.2: 40 h / 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; dichloromethane; toluene; 2.1: Mannich reaction / 2.2: Mannich reaction;

DOI:10.1021/ol201349k

Reference yield: 71.0%

(3S,4R,E)-4-(allyl(benzyl)amino)-2-methyl-6-phenylhex-5-en-3-ol (1313436-00-8) → (S)-1-((R)-1-benzyl-2,5-dihydro-1H-pyrrol-2-yl)-2-methylpropan-1-ol

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; Inert atmosphere; Reflux;

DOI:10.1021/ol201349k

upstream raw materials:

Allylbenzylamine

(2S)-2-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanal

4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane

(S)-methyl 2-(tert-butyldiphenylsilyloxy)-3-methylbutanoate