(6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic acid methyl ester

Base Information

• Chemical Name: (6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic acid methyl ester
• CAS No.: 298691-07-3
• Molecular Formula: C₃₅H₄₄O₆SSi
• Molecular Weight: 620.882

Synonyms:(6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic acid methyl ester

Chemical Property of (6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic acid methyl ester

There total 9 articles about (6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic 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: 82.0%

p-toluenesulfonyl chloride (98-59-9) + (6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-hydroxy-undeca-6,8-dienoic acid methyl ester (298691-16-4) → (6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic acid methyl ester (298691-07-3)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(00)00971-0

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic acid methyl ester (298691-07-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

2: 100 percent / H₅IO₆ / diethyl ether; tetrahydrofuran / 0.25 h / 0 °C

3: 85 percent / benzene / 4 h / Heating

4: 100 percent / H₂ / Pd/C

5: 92 percent / H₅IO₆ / diethyl ether; tetrahydrofuran / 18 h / 20 °C

6: 78 percent / benzene / Heating

7: 90 percent / LHDMS / -78 - 20 °C

8: 48 percent / 1N HCl / tetrahydrofuran; H₂O / 40 h / 20 °C

9: 82 percent / pyridine / 0 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; hydrogen; periodic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene; 1: silylation / 2: Oxidation / 3: Condensation / 4: Catalytic hydrogenation / 5: Oxidation / 6: Condensation / 7: Condensation / 8: ether cleavage / 9: Esterification;

DOI:10.1016/S0040-4039(00)00971-0

Reference yield:

3-(tert-butyl-diphenyl-silanyloxy)-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde → (6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-(toluene-4-sulfonyloxy)-undeca-6,8-dienoic acid methyl ester (298691-07-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / benzene / 4 h / Heating

2: 100 percent / H₂ / Pd/C

3: 92 percent / H₅IO₆ / diethyl ether; tetrahydrofuran / 18 h / 20 °C

4: 78 percent / benzene / Heating

5: 90 percent / LHDMS / -78 - 20 °C

6: 48 percent / 1N HCl / tetrahydrofuran; H₂O / 40 h / 20 °C

7: 82 percent / pyridine / 0 - 20 °C

With pyridine; hydrogenchloride; hydrogen; periodic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; benzene; 1: Condensation / 2: Catalytic hydrogenation / 3: Oxidation / 4: Condensation / 5: Condensation / 6: ether cleavage / 7: Esterification;

DOI:10.1016/S0040-4039(00)00971-0

upstream raw materials:

p-toluenesulfonyl chloride

(6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-hydroxy-undeca-6,8-dienoic acid methyl ester

tert-butylchlorodiphenylsilane

methyl 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate

Downstream raw materials:

(6E,8Z,11Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-20-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-icosa-6,8,11-trienoic acid

(6E,8Z,11Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-20-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-icosa-6,8,11-trienoic acid methyl ester

(6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

(6E,8Z,11Z)-(S)-20-Amino-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

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