(12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester

Base Information

Chemical Name:(12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester
CAS No.:863604-43-7
Molecular Formula:C₃₈H₅₈O₄Si
Molecular Weight:606.962
Hs Code.:

Synonyms:(12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester

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Chemical Property of (12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester

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Technology Process of (12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester

There total 11 articles about (12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl 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: 88.0%

: 863604-42-6
(12R)-2,2-dimethylpropionic acid 1,13-epoxytridecyl ester

: 380893-75-4
(R)-(but-3-yn-2-yloxy)(tert-butyl)diphenylsilane

: 863604-43-7
(12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester

Guidance literature:: (R)-(but-3-yn-2-yloxy)(tert-butyl)diphenylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(12R)-2,2-dimethylpropionic acid 1,13-epoxytridecyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1021/ja051986l

Reference yield:

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

: 863604-43-7
(12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester

Guidance literature:: Multi-step reaction with 6 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

With pyridine; dmap; n-butyllithium; hydrogen; silica gel; iron(III) chloride; 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

: 863604-43-7
(12R,16R)-2,2-dimethylpropionic acid 16-(tert-butyldiphenylsilanyloxy)-12-hydroxyheptadec-14-ynyl ester

Guidance literature:: Multi-step reaction with 7 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

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