(–)-(1S,2E,S_S)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane

Base Information

• Chemical Name: (–)-(1S,2E,S_S)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane
• CAS No.: 1291100-09-8
• Molecular Formula: C₃₁H₄₆O₂SSi
• Molecular Weight: 510.857

Synonyms:(–)-(1S,2E,S_S)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane

Chemical Property of (–)-(1S,2E,S_S)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane

Chemical Property:

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Technology Process of (–)-(1S,2E,S_S)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane

There total 2 articles about (–)-(1S,2E,S_S)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane 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: 80.0%

tributylchlorosilane (995-45-9) + (–)-(1S,2E,SS)-4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-ol (1291100-05-4) → (–)-(1S,2E,SS)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane (1291100-09-8)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 72h; Inert atmosphere;

DOI:10.1021/ol200718y

Reference yield:

C12H14OS (1092556-87-0) → (–)-(1S,2E,SS)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane (1291100-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: dmap; triethylamine / N,N-dimethyl-formamide / 72 h / 0 - 20 °C / Inert atmosphere

With dmap; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ol200718y

Reference yield:

piperidine (110-89-4) + (–)-(1S,2E,SS)-tributyl [4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-yloxy]silane (1291100-09-8) → (+)-(2S,3E,5R)-2-methyl-5-phenyl-1-(piperidin-1-yl)-5-(tributylsilyloxy)pent-3-en-2-ol (1291100-21-4) + (+)-(2R,3E,5R)-2-methyl-5-phenyl-1-(piperidin-1-yl)-5-(tributylsilyloxy)pent-3-en-2-ol

Guidance literature:

In ethanol; at 70 ℃; for 120h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol200718y

upstream raw materials:

C₁₂H₁₄OS

tributylchlorosilane

(–)-(1S,2E,S_S)-4-methyl-1-phenyl-2-(p-tolylsulfinyl)penta-2,4-dien-1-ol

Downstream raw materials:

(+)-(2S,3E,5R)-2-methyl-5-phenyl-1-(piperidin-1-yl)-5-(tributylsilyloxy)pent-3-en-2-ol

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