(2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl ester

Base Information

• Chemical Name: (2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl ester
• CAS No.: 176900-65-5
• Molecular Formula: C₂₄H₃₂O₃Si
• Molecular Weight: 396.602
• Mol file: 176900-65-5.mol

Synonyms:(2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl ester

Chemical Property of (2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl ester

There total 9 articles about (2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl 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: 100.0%

(R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-methylene-pentanoic acid methyl ester (176900-64-4) → (2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl ester (176900-65-5)

Guidance literature:

With rhodium(III) chloride; In ethanol; for 5h; Heating;

DOI:10.1016/0968-0896(96)00014-4

Reference yield: 87.0%

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → (2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl ester (176900-65-5)

Guidance literature:

In toluene; at 80 ℃; for 16h;

DOI:10.1002/anie.200603635

Reference yield:

2,4-dimethylpentane-1,5-diol (2121-69-9) → (2E,4S)-2,4-dimethyl-5-(tert-butyldiphenylsilyloxy)-2-pentanoic acid methyl ester (176900-65-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 50 percent / tetrahydrofuran; H₂O / 8 h / 28 °C / porcine pancreatic lipase

2: 98 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

3: 95 percent / aq. K₂CO₃ / methanol / 2 h / 40 °C

4: Jones reagent / acetone / 0.5 h / 0 °C

5: aq. NaOH / diethyl ether / 0.5 h / 0 °C

6: 1.) LDA, 2.) PhSeBr, 3.) 30percent aq. H₂O₂, pyridine

With pyridine; 1H-imidazole; sodium hydroxide; jones reagent; Phenylselenyl bromide; dihydrogen peroxide; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0968-0896(96)00014-4

upstream raw materials:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

methyl 2-(triphenylphosphoranylidene)propionate

(R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-methylene-pentanoic acid methyl ester

(2S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-pentanoic acid methyl ester

Downstream raw materials:

(E)-(2R,4R,5R,8R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2,6,8-trimethyl-non-6-en-3-one

(R,E)-5-(((tert-butyl)diphenylsilyl)oxy)-2,4-dimethylpent-2-enal

(E)-(R)-5-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-en-1-ol