(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol

Base Information

• Chemical Name: (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol
• CAS No.: 225114-87-4
• Molecular Formula: C₂₄H₃₄O₂Si₂
• Molecular Weight: 410.704
• Mol file: 225114-87-4.mol

Synonyms:(S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol

Chemical Property of (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol

There total 9 articles about (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-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: 93.0%

5-(tert-Butyl-diphenyl-silanyloxy)-1-trimethylsilanyl-pent-1-yn-3-one (105198-76-3) → (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol (225114-87-4)

Guidance literature:

With Noyori's catalyst; In isopropyl alcohol; at 20 ℃; for 0.5h;

DOI:10.1021/acs.joc.8b03249

Reference yield: 80.0%

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) + trimethylsilylacetylene (1066-54-2) → (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol (225114-87-4)

Guidance literature:

trimethylsilylacetylene; With titanium(IV) isopropylate; diethylzinc; (R)-1,1'-Bi-2-naphthol; In N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; at 20 ℃; for 2h;

3-(tert-butyldiphenylsilyloxy)-1-propanal; With titanium(IV) isopropylate; In N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; at 20 ℃; for 12h; enantioselective reaction;

DOI:10.1055/s-0033-1339493

Reference yield:

3-(tert-butyldiphenylsilyloxy)propan-1-ol (127047-71-6) → (S)-5-((tert-butyldiphenylsilyl)oxy)-1-(trimethylsilyl)pent-1-yn-3-ol (225114-87-4)

Guidance literature:

Multi-step reaction with 4 steps

1: DMSO; (COCl)2 / tetrahydrofuran

2: tetrahydrofuran

3: DMSO; (COCl)2 / tetrahydrofuran

4: 9-borabicyclo<3.3.1>nonane; (S)-(-)-α-pinene / tetrahydrofuran

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; (-)-α-pinene; dimethyl sulfoxide; In tetrahydrofuran; 1: Oxidation / 2: Condensation / 3: Oxidation / 4: Reduction;

DOI:10.1039/a807074a

upstream raw materials:

5-(tert-Butyl-diphenyl-silanyloxy)-1-trimethylsilanyl-pent-1-yn-3-one

3-(tert-butyldiphenylsilyloxy)-1-propanal

3-(tert-butyldiphenylsilyloxy)propan-1-ol

tert-butylchlorodiphenylsilane

Downstream raw materials:

C₂₆H₃₈O₃Si₂

5-(tert-butyl-diphenyl-silanyloxy)-pent-1-yn-3-ol

C₂₃H₃₀O₃Si

C₂₃H₂₉BrO₃SiZn