(4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole

Base Information

• Chemical Name: (4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole
• CAS No.: 716369-46-9
• Molecular Formula: C₂₈H₃₉NO₂SeSi
• Molecular Weight: 528.669
• Mol file: 716369-46-9.mol

Synonyms:(4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole

Chemical Property of (4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole

There total 7 articles about (4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole 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: 71.0%

Cinnamyl bromide (4392-24-9) + 2-(2-bromo-phenyl)-(4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-4,5-dihydro-oxazole (716369-44-7) → (4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole (716369-46-9)

Guidance literature:

2-(2-bromo-phenyl)-(4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-4,5-dihydro-oxazole; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 1h;

With selenium; In tetrahydrofuran; pentane; at -78 - 0 ℃; for 2h;

Cinnamyl bromide; In tetrahydrofuran; pentane; at 0 ℃; for 1h;

DOI:10.1039/b316502g

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole (716369-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C

2.2: Se / tetrahydrofuran; pentane / 2 h / -78 - 0 °C

2.3: 71 percent / tetrahydrofuran; pentane / 1 h / 0 °C

With 2,6-dimethylpyridine; tert.-butyl lithium; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1039/b316502g

Reference yield:

2-bromobenzoic acid chloride (7154-66-7) → (4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-[2-(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazole (716369-46-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 72 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

2.1: 91 percent / DAST / CH₂Cl₂ / 1 h / -78 °C

3.1: 74 percent / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

4.1: 58 percent / NaBH₄ / methanol / 0.5 h / 20 °C

5.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C

6.2: Se / tetrahydrofuran; pentane / 2 h / -78 - 0 °C

6.3: 71 percent / tetrahydrofuran; pentane / 1 h / 0 °C

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; tert.-butyl lithium; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane;

DOI:10.1039/b316502g

upstream raw materials:

Cinnamyl bromide

2-(2-bromo-phenyl)-(4S)-[(1S)-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-4,5-dihydro-oxazole

t-butyldimethylsiyl triflate

2-bromobenzoic acid chloride

Downstream raw materials:

(1S)-1-phenylprop-2-en-1-ol

(R)-1-phenylprop-2-en-1-ol

2-methyl-1-{2-[(3-phenyl-(E)-allylselanyl)-phenyl]-4,5-dihydro-oxazol-(4S)-yl}-propan-(1S)-ol