(S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol

Base Information

• Chemical Name: (S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol
• CAS No.: 1380215-37-1
• Molecular Formula: C₁₈H₂₅NO₂S
• Molecular Weight: 319.468
• Mol file: 1380215-37-1.mol

Synonyms:(S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol

Chemical Property of (S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol

There total 1 articles about (S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-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: 73.0%

4-pentenal (2100-17-6) + (+)-(S)-S-(1-cyclopen-1-ylmethyl)-N-methyl-S-phenylsulfoximine (131865-69-5) → 1-((-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol + (S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol (1380215-37-1)

Guidance literature:

(+)-(S)-S-(1-cyclopen-1-ylmethyl)-N-methyl-S-phenylsulfoximine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

With triisopropoxytitanium(IV) chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h; Inert atmosphere;

4-pentenal; In tetrahydrofuran; hexane; at -78 ℃; for 2.75h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201103060

Reference yield: 83.0%

triethylsilyl chloride (994-30-9) + (S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol (1380215-37-1) → triethyl(S)-1-((((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-enyloxy)silane (1380215-38-2)

Guidance literature:

(S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol; With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1h; Inert atmosphere;

triethylsilyl chloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/chem.201103060

Reference yield:

(S)-1-(((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-en-1-ol (1380215-37-1) → (S)-1-((1R,3R,E)-2[(S)-N-methyl-S-phenylsulfonimidoyl])-3-((S)-1-(triethylsilyloxy)pent-4-enyl)cyclopentenylpent-4-en-1-ol

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

1.2: 20 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 - 20 °C / Inert atmosphere

2.3: 2.75 h / -78 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201103060

upstream raw materials:

4-pentenal

(+)-(S)-S-(1-cyclopen-1-ylmethyl)-N-methyl-S-phenylsulfoximine

Downstream raw materials:

triethyl((S)-1-(((R)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopent-2-enyl)pent-4-enyloxy)silane

triethyl(S)-1-((((R,Z)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylene)cyclopentyl)pent-4-enyloxy)silane