(-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester

Base Information

• Chemical Name: (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester
• CAS No.: 948859-76-5
• Molecular Formula: C₄₆H₇₂O₄SSi
• Molecular Weight: 749.227

Synonyms:(-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester

Chemical Property of (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester

There total 25 articles about (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl 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: 99.0%

(-)-(3R,5R,7R,9S,11S,13S,15S)-16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecan-1-ol (948859-75-4) + p-toluenesulfonyl chloride (98-59-9) → (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester (948859-76-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ol071078o

Reference yield:

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester (917590-73-9) → (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester (948859-76-5)

Guidance literature:

Multi-step reaction with 22 steps

1.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

1.2: 95 percent / diethyl ether; various solvent(s) / 17 h / -75 °C

2.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

3.1: 1.491 g / CH₂Cl₂ / 24 h / Heating

4.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

4.2: diethyl ether; various solvent(s) / 17 h / -75 °C

5.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

6.1: CH₂Cl₂ / 24 h / Heating

7.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

7.2: diethyl ether; various solvent(s) / 17 h / -75 °C

8.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

9.1: CH₂Cl₂ / 24 h / Heating

10.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

10.2: diethyl ether; various solvent(s) / 17 h / -75 °C

11.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

12.1: CH₂Cl₂ / 24 h / Heating

13.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

13.2: diethyl ether; various solvent(s) / 17 h / -75 °C

14.1: DIBALH / tetrahydrofuran; toluene / -70 °C

15.1: CH₂Cl₂ / 24 h / Heating

16.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

16.2: diethyl ether; various solvent(s) / 17 h / -75 °C

17.1: DIBALH / CH₂Cl₂; toluene / -70 °C

18.1: CH₂Cl₂ / 24 h / Heating

19.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

19.2: diethyl ether; various solvent(s) / 17 h / -75 °C

20.1: DIBALH / CH₂Cl₂ / -50 °C

21.1: 76 mg / DIBALH / CH₂Cl₂ / -50 °C

22.1: 99 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; triethylsilane; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 3.1: Wittig reaction / 6.1: Wittig reaction / 9.1: Wittig reaction / 12.1: Wittig reaction / 15.1: Wittig reaction / 18.1: Wittig reaction;

DOI:10.1021/ol071078o

Reference yield:

(-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester (948859-73-2) → (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester (948859-76-5)

Guidance literature:

Multi-step reaction with 19 steps

1.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

1.2: diethyl ether; various solvent(s) / 17 h / -75 °C

2.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

3.1: CH₂Cl₂ / 24 h / Heating

4.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

4.2: diethyl ether; various solvent(s) / 17 h / -75 °C

5.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

6.1: CH₂Cl₂ / 24 h / Heating

7.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

7.2: diethyl ether; various solvent(s) / 17 h / -75 °C

8.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

9.1: CH₂Cl₂ / 24 h / Heating

10.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

10.2: diethyl ether; various solvent(s) / 17 h / -75 °C

11.1: DIBALH / tetrahydrofuran; toluene / -70 °C

12.1: CH₂Cl₂ / 24 h / Heating

13.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

13.2: diethyl ether; various solvent(s) / 17 h / -75 °C

14.1: DIBALH / CH₂Cl₂; toluene / -70 °C

15.1: CH₂Cl₂ / 24 h / Heating

16.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

16.2: diethyl ether; various solvent(s) / 17 h / -75 °C

17.1: DIBALH / CH₂Cl₂ / -50 °C

18.1: 76 mg / DIBALH / CH₂Cl₂ / -50 °C

19.1: 99 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; triethylsilane; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 3.1: Wittig reaction / 6.1: Wittig reaction / 9.1: Wittig reaction / 12.1: Wittig reaction / 15.1: Wittig reaction;

DOI:10.1021/ol071078o

upstream raw materials:

(-)-(3R,5R,7R,9S,11S,13S,15S)-16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecan-1-ol

p-toluenesulfonyl chloride

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester

(-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester

Downstream raw materials:

(-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane

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