(3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-ol

Base Information

• Chemical Name: (3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-ol
• CAS No.: 863604-53-9
• Molecular Formula: C₅₀H₇₈O₃Si₃
• Molecular Weight: 811.424
• Mol file: 863604-53-9.mol

Synonyms:(3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-ol

Chemical Property of (3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-ol

There total 16 articles about (3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-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:

(4R)-11-(2,2-dimethyl-[1,3]dioxolan-4-yl)undec-10-en-1-ol → (3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-ol (863604-53-9)

Guidance literature:

Multi-step reaction with 10 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

9.1: 97 percent / DMSO; diisopropylethylamine; SO₃*pyridine / CH₂Cl₂ / 1 h / 0 °C

10.1: BF₃*Et₂O / tetrahydrofuran; hexane / 0.08 h / -78 °C

10.2: tetrahydrofuran; hexane / 4 h / -78 °C

10.3: 340 mg / aq. H₂O₂ / tetrahydrofuran; hexane; aq. phosphate buffer / 16 h / 20 °C

With pyridine; dmap; n-butyllithium; pyridine-SO₃ complex; boron trifluoride diethyl etherate; hydrogen; silica gel; iron(III) chloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; 9.1: Parikh-Doering oxidation;

DOI:10.1021/ja051986l

Reference yield:

1-(tert-butyldiphenylsilanyl)-11-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]undec-10-en-1-ol → (3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-ol (863604-53-9)

Guidance literature:

Multi-step reaction with 11 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

10.1: 97 percent / DMSO; diisopropylethylamine; SO₃*pyridine / CH₂Cl₂ / 1 h / 0 °C

11.1: BF₃*Et₂O / tetrahydrofuran; hexane / 0.08 h / -78 °C

11.2: tetrahydrofuran; hexane / 4 h / -78 °C

11.3: 340 mg / aq. H₂O₂ / tetrahydrofuran; hexane; aq. phosphate buffer / 16 h / 20 °C

With pyridine; dmap; n-butyllithium; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; silica gel; iron(III) chloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; 10.1: Parikh-Doering oxidation;

DOI:10.1021/ja051986l

Reference yield:

(10-((tert-butyldiphenylsilyl)oxy)decyl)triphenylphosphonium iodide → (3S,4R,15R,19R)-15-(tert-butyldimethylsilanyloxy)-19-(tert-butyldiphenylsilanyloxy)-3-(dimethylphenylsilanyl)eicos-1-en-17-yn-4-ol (863604-53-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

1.2: 8.9 g / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 92 percent / TBAF / tetrahydrofuran / 20 h / 20 °C

3.1: 85 percent / hydrogen / Pd/C / tetrahydrofuran; ethanol / 2 h / 20 °C

4.1: 93 percent / pyridine; DMAP / CH₂Cl₂ / 20 h / 20 °C

5.1: 62 percent / FeCl₃*6H₂O*SiO₂ / CHCl₃ / 168 h / 20 °C

6.1: 83 percent / dibutyltin oxide; triethylamine / CH₂Cl₂ / 16 h / 20 °C

7.1: 100 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

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

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

8.3: 88 percent / tetrahydrofuran; hexane / 1 h / -78 °C

9.1: 93 percent / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

10.1: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

11.1: 97 percent / DMSO; diisopropylethylamine; SO₃*pyridine / CH₂Cl₂ / 1 h / 0 °C

12.1: BF₃*Et₂O / tetrahydrofuran; hexane / 0.08 h / -78 °C

12.2: tetrahydrofuran; hexane / 4 h / -78 °C

12.3: 340 mg / aq. H₂O₂ / tetrahydrofuran; hexane; aq. phosphate buffer / 16 h / 20 °C

With pyridine; dmap; n-butyllithium; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; silica gel; iron(III) chloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; 1.2: Wittig reaction / 11.1: Parikh-Doering oxidation;

DOI:10.1021/ja051986l

upstream raw materials:

(12R,16R)-12-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-ynal

[(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane

(4R)-11-(2,2-dimethyl-[1,3]dioxolan-4-yl)undecan-1-ol

(12R)-2,2-dimethylpropionic acid 1,13-epoxytridecyl ester

Downstream raw materials:

(+)-asimicin

(2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran

Refernces