(12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol

Base Information

Chemical Name:(12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol
CAS No.:863604-52-8
Molecular Formula:C₃₉H₆₄O₃Si₂
Molecular Weight:637.106
Hs Code.:

Synonyms:(12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol

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Chemical Property of (12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol

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Technology Process of (12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol

There total 13 articles about (12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol 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: 97.0%

: 863604-51-7
(12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-(tert-budyldimethylsilanyloxy)heptadec-14-ynyl ester

: 863604-52-8
(12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ja051986l

Reference yield:

: (4R)-11-(2,2-dimethyl-[1,3]dioxolan-4-yl)undec-10-en-1-ol

: 863604-52-8
(12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 85 percent / hydrogen / Pd/C / tetrahydrofuran; ethanol / 2 h / 20 °C

2.1: 93 percent / pyridine; DMAP / CH₂Cl₂ / 20 h / 20 °C

3.1: 62 percent / FeCl₃*6H₂O*SiO₂ / CHCl₃ / 168 h / 20 °C

4.1: 83 percent / dibutyltin oxide; triethylamine / CH₂Cl₂ / 16 h / 20 °C

5.1: 100 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: BF₃*OEt₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.3: 88 percent / tetrahydrofuran; hexane / 1 h / -78 °C

7.1: 93 percent / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

8.1: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

With pyridine; dmap; n-butyllithium; hydrogen; silica gel; iron(III) chloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform;
DOI:10.1021/ja051986l

Reference yield:

: 1-(tert-butyldiphenylsilanyl)-11-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]undec-10-en-1-ol

: 863604-52-8
(12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yn-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 92 percent / TBAF / tetrahydrofuran / 20 h / 20 °C

2.1: 85 percent / hydrogen / Pd/C / tetrahydrofuran; ethanol / 2 h / 20 °C

3.1: 93 percent / pyridine; DMAP / CH₂Cl₂ / 20 h / 20 °C

4.1: 62 percent / FeCl₃*6H₂O*SiO₂ / CHCl₃ / 168 h / 20 °C

5.1: 83 percent / dibutyltin oxide; triethylamine / CH₂Cl₂ / 16 h / 20 °C

6.1: 100 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: BF₃*OEt₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.3: 88 percent / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: 93 percent / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

9.1: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

With pyridine; dmap; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; silica gel; iron(III) chloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform;
DOI:10.1021/ja051986l