(+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine

Base Information

• Chemical Name: (+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine
• CAS No.: 473434-00-3
• Molecular Formula: C₂₇H₄₁NO₂SSi
• Molecular Weight: 471.78
• Mol file: 473434-00-3.mol

Synonyms:(+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine

Chemical Property of (+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine

There total 1 articles about (+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine 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: 99.0%

triethylsilyl chloride (994-30-9) + (+)-(3S,4R,5Z)-2,5-dimethyl-6-[(S)-N-methyl-S-phenylsulfonimidoyl]-4-phenyl-5-hexen-3-ol (573681-21-7) → (+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine (473434-00-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200390210

Reference yield: 93.0%

(+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine (473434-00-3) → (+)-(S)-S-[(1E,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)-1-hexenyl]-N-methyl-S-phenylsulfoximine

Guidance literature:

With methyllithium; In diethyl ether; at -35 ℃; for 2h;

DOI:10.1002/ejoc.200390210

Reference yield:

(+)-(S)-S-[(1Z,3R,4S)-2,5-dimethyl-3-phenyl-4-(triethylsilyloxy)hex-1-enyl]-N-methyl-S-phenylsulfoximine (473434-00-3) → (S)-methylphenylsulfoxide (1193-82-4,4850-71-9,18453-46-8,20696-08-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 93 percent / MeLi / diethyl ether / 2 h / -35 °C

2.1: 82 percent / aq. HCl / tetrahydrofuran; acetic acid / 2 h / 20 °C

3.1: tetrahydrofuran / 2 h / 20 °C

3.2: 95 percent / aq. NH₃ / 1 h / 20 °C

4.1: 10 percent / nBuLi / hexane; tetrahydrofuran / 18 h / -78 - 20 °C

5.1: nBuLi; ClTi(OiPr)3 / hexane; tetrahydrofuran / 1.08 h / -78 - 0 °C

5.2: 59 percent / 1.33 h / -78 °C

6.1: tetrahydrofuran / 2 h / 20 °C

6.2: 89 percent / aq. NH₃ / 1 h / 20 °C

7.1: 84 percent / nBuLi / hexane; tetrahydrofuran / 18 h / -78 - 20 °C

8.1: 73 percent / nBuLi / tetrahydrofuran; hexane / 3.5 h / -78 °C

9.1: 70 percent / tetrahydrofuran / 0.75 h / -78 °C

With triisopropoxytitanium(IV) chloride; hydrogenchloride; n-butyllithium; methyllithium; In tetrahydrofuran; diethyl ether; hexane; acetic acid;

DOI:10.1002/ejoc.200390210

upstream raw materials:

triethylsilyl chloride

(+)-(3S,4R,5Z)-2,5-dimethyl-6-[(S)-N-methyl-S-phenylsulfonimidoyl]-4-phenyl-5-hexen-3-ol

Downstream raw materials:

(S)-methylphenylsulfoxide

C₆H₅C₁₀H₁₂SON

(-)-(S,Z)-N-methyl-S-(2-methyl-3-phenyl-2-propenyl)-S-phenylsulfoximine

(+)-(S,E)-N-methyl-S-(2-methyl-3-phenyl-2-propenyl)-S-phenylsulfoximine