Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester
• CAS No.: 321162-62-3
• Molecular Formula: C₃₁H₄₀O₄SSi
• Molecular Weight: 536.808
• Mol file: 321162-62-3.mol

Synonyms:Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester

Chemical Property of Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester

There total 1 articles about Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester 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:

p-toluenesulfonyl chloride (98-59-9) + (3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol (198124-61-7) → Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester (321162-62-3)

Guidance literature:

(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

p-toluenesulfonyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ja005526y DOI:10.1016/j.tet.2004.06.014

Reference yield: 63.0%

Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester (321162-62-3) → (2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene (320742-72-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1.5h; Heating;

DOI:10.1016/j.tet.2004.06.014

Reference yield:

Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester (321162-62-3) → (R)-N,2-dimethyl-N-((3S,5S,6R)-3,5,6-trimethyl-8-oxo-8-((R)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide (320742-82-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 63 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

2.2: 71 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

4.1: 87 percent / NaN₃ / dimethylformamide / 20 °C

5.1: H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

6.1: 93 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 0 - 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

7.2: 83 percent / tetrahydrofuran / -78 - 20 °C

8.1: 94 percent / TBAF / tetrahydrofuran / 0 - 20 °C

9.1: DMSO; Et₃N; sulfur trioxide*pyridine / CH₂Cl₂ / 0 - 20 °C

10.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

10.2: 195 mg / tetrahydrofuran / 2 h / 0 °C

11.1: CuBr*Me₂S; Me₂S / tetrahydrofuran / 0.67 h / -78 - 0 °C

11.2: 96 percent / tetrahydrofuran; CH₂Cl₂ / 2.5 h / -78 - -30 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; sodium azide; copper(I) bromide dimethylsulfide complex; dimethylsulfide; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 10.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2004.06.014

upstream raw materials:

p-toluenesulfonyl chloride

(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol

Downstream raw materials:

(2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene

(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol

(3S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexylamine

(2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane