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

Base Information

• Chemical Name: (-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane
• CAS No.: 948859-77-6
• Molecular Formula: C₅₃H₉₄OSi
• Molecular Weight: 775.414

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 26 articles about (-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane 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: 75.0%

(-)-(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) + 1-Bromotetradecane (112-71-0) → (-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane (948859-77-6)

Guidance literature:

1-Bromotetradecane; With magnesium; In tetrahydrofuran; at 45 ℃; for 1h;

(-)-(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; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at 20 ℃; for 24h; Further stages.;

DOI:10.1021/ol071078o

Reference yield:

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester (917590-73-9) → (-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane (948859-77-6)

Guidance literature:

Multi-step reaction with 23 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

23.1: magnesium / tetrahydrofuran / 1 h / 45 °C

23.2: 75 percent / CuBr*SMe₂ / tetrahydrofuran / 24 h / 20 °C

With pyridine; triethylsilane; diisobutylaluminium hydride; magnesium; 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) → (-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane (948859-77-6)

Guidance literature:

Multi-step reaction with 20 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

20.1: magnesium / tetrahydrofuran / 1 h / 45 °C

20.2: 75 percent / CuBr*SMe₂ / tetrahydrofuran / 24 h / 20 °C

With pyridine; triethylsilane; diisobutylaluminium hydride; magnesium; 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)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester

1-Bromotetradecane

(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

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