(2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol

Base Information

• Chemical Name: (2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol
• CAS No.: 155486-94-5
• Molecular Formula: C₁₈H₃₂O₂SSi
• Molecular Weight: 340.602
• Mol file: 155486-94-5.mol

Synonyms:(2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol

Chemical Property of (2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol

There total 2 articles about (2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol 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: 46.0%

hexanal (66-25-1) + (RS)-p-Tolyl β-(trimethylsilyl)ethyl sulfoxide (153123-09-2) → (2R,3R)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol (155394-02-8) + (2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol (155486-94-5)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

DOI:10.1016/S0040-4020(01)80816-4

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol (155486-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / diisopropylamine, butyllithium / tetrahydrofuran; hexane / 2 h / -78 deg C to r.t.

2: 46 percent / diisopropylamine, butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(01)80816-4

Reference yield: 91.0%

(2R,3S)-2-<(R)-p-tolylsulfinyl>-1-(trimethylsilyl)-3-octanol (155486-94-5) → (S)-oct-1-en-3-ol (3391-86-4,3687-48-7,50999-79-6,24587-53-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80816-4

upstream raw materials:

hexanal

(R_S)-p-Tolyl β-(trimethylsilyl)ethyl sulfoxide

(R)-methyl p-tolyl sulfoxide

Downstream raw materials:

(S)-oct-1-en-3-ol