(2R,5S,S_S)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-ol

Base Information

• Chemical Name: (2R,5S,S_S)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-ol
• CAS No.: 773900-55-3
• Molecular Formula: C₃₅H₄₀O₃SSi
• Molecular Weight: 568.852

Synonyms:(2R,5S,S_S)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-ol

Chemical Property of (2R,5S,S_S)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-ol

Chemical Property:

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Technology Process of (2R,5S,S_S)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-ol

There total 1 articles about (2R,5S,S_S)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-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: 57.0%

Triphenylsilyl chloride (76-86-8) + (+)-(2R,5S,SS)-(3E)-2-methyl-4-(p-tolylsulfinyl)non-3-en-1,5-diol (773900-47-3) → (2R,5S,SS)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-ol (773900-55-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tet.2004.06.092

Reference yield: 64.0%

methanesulfonyl chloride (124-63-0) + (2R,5S,SS)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-ol (773900-55-3) → Methanesulfonic acid (E)-(1S,4R)-1-butyl-4-methyl-2-((S)-toluene-4-sulfinyl)-5-triphenylsilanyloxy-pent-2-enyl ester (773900-56-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 1 ℃; for 0h;

DOI:10.1016/j.tet.2004.06.092

Reference yield:

(2R,5S,SS)-(3E)-2-methyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-3-en-5-ol (773900-55-3) → (2R,3S,SS)-(4E)-2,3-dimethyl-4-(p-tolylsulfinyl)-1-triphenylsilyloxynon-4-ene

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / Et₃N / tetrahydrofuran / 0 h / 1 °C

2: 76 percent / CuCN / tetrahydrofuran / 40.5 h / 0 - 20 °C

With triethylamine; In tetrahydrofuran;

DOI:10.1016/j.tet.2004.06.092

upstream raw materials:

Triphenylsilyl chloride

(+)-(2R,5S,S_S)-(3E)-2-methyl-4-(p-tolylsulfinyl)non-3-en-1,5-diol

Downstream raw materials:

Methanesulfonic acid (E)-(1S,4R)-1-butyl-4-methyl-2-((S)-toluene-4-sulfinyl)-5-triphenylsilanyloxy-pent-2-enyl ester

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