N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide
• CAS No.: 143371-18-0
• Molecular Formula: C₃₂H₃₉NO₅S
• Molecular Weight: 549.731
• Mol file: 143371-18-0.mol

Synonyms:N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

Chemical Property of N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

There total 3 articles about N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide 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:

{(S)-3-[(4-Methoxy-benzyl)-(toluene-4-sulfonyl)-amino]-3-phenyl-propyl}-triphenyl-phosphonium; iodide (124944-47-4) → N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide (143371-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium, LiBr / tetrahydrofuran / 0.75 h / 0 °C

2: 2.) phenyllithium, 3.) t-BuOK

With n-butyllithium; potassium tert-butylate; phenyllithium; lithium bromide; In tetrahydrofuran;

DOI:10.1021/ja00047a008

Reference yield:

methyl 3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate (90472-93-8) → N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide (143371-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / diisobutylaluminum hydride (DIBAL) / CH₂Cl₂; hexane / 0.12 h / -78 °C

2: 2.) phenyllithium, 3.) t-BuOK

With potassium tert-butylate; diisobutylaluminium hydride; phenyllithium; In hexane; dichloromethane;

DOI:10.1021/ja00047a008

Reference yield:

(4S)-4,5-(isopropylidenedioxy)-1-pentanal (42890-81-3) + N-(4-Methoxy-benzyl)-4-methyl-N-[(S)-1-phenyl-3-(triphenyl-λ5-phosphanylidene)-propyl]-benzenesulfonamide → N-[(Z)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide (143371-17-9) + N-[(E)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-hex-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide (143371-18-0)

Guidance literature:

With potassium tert-butylate; phenyllithium; Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/ja00047a008

upstream raw materials:

(4S)-4,5-(isopropylidenedioxy)-1-pentanal

{(S)-3-[(4-Methoxy-benzyl)-(toluene-4-sulfonyl)-amino]-3-phenyl-propyl}-triphenyl-phosphonium; iodide

methyl 3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate

Downstream raw materials:

N-((E)-(1S,7S)-7,8-Dihydroxy-1-phenyl-oct-3-enyl)-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

N-((E)-(1S,7S)-8-[1,3]Dithian-2-yl-7-hydroxy-1-phenyl-oct-3-enyl)-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

N-[(E)-(1S,7S)-7-(tert-Butyl-diphenyl-silanyloxy)-8-[1,3]dithian-2-yl-1-phenyl-oct-3-enyl]-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide

2,4,6-Trimethyl-benzenesulfonic acid (E)-(2S,8S)-2-hydroxy-8-[(4-methoxy-benzyl)-(toluene-4-sulfonyl)-amino]-8-phenyl-oct-5-enyl ester