(1S,2R,R_S)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol

Base Information

• Chemical Name: (1S,2R,R_S)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol
• CAS No.: 304881-56-9
• Molecular Formula: C₂₆H₃₈O₃SSi
• Molecular Weight: 458.737

Synonyms:(1S,2R,R_S)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol

Chemical Property of (1S,2R,R_S)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol

Chemical Property:

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Technology Process of (1S,2R,R_S)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol

There total 1 articles about (1S,2R,R_S)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-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: 48.0%

(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde (133187-22-1) + 1-Methyl-4-((R)-(E)-3-methyl-but-1-ene-1-sulfinyl)-benzene → (-)-(1S,2S,RS)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol + (1S,2R,RS)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol (304881-56-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo000468k

Reference yield:

(1S,2R,RS)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol (304881-56-9) → (-)-(1S,2S,RS)-(3E)-1,2-epoxy-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-ene

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 3 h / 0 - 20 °C

2: 30 mg / TBAF / tetrahydrofuran / 0.08 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1: Condensation / 2: Elimination;

DOI:10.1021/jo000468k

Reference yield:

(1S,2R,RS)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2-ol (304881-56-9) + Methanesulfonic anhydride (7143-01-3) → mesylate of (-)-(1S,2R,RS)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2ol (304882-03-9)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo000468k

upstream raw materials:

(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde

Downstream raw materials:

mesylate of (-)-(1S,2R,R_S)-(3E)-1-[(tert-butyldimethylsilyl)oxy]-5-methyl-1-phenyl-3-(p-tolylsulfinyl)hex-3-en-2ol

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