(S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole

Base Information

• Chemical Name: (S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole
• CAS No.: 142075-81-8
• Molecular Formula: C₂₇H₄₇NO₃Si₂
• Molecular Weight: 489.846
• Mol file: 142075-81-8.mol

Synonyms:(S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole

Chemical Property of (S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole

There total 5 articles about (S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-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: 65.0%

(2S,3S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanal (142075-75-0) + 1,1-dibromomethane (74-95-3) → (S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole (142075-81-8)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)79046-0

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole (142075-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Et₃N, 2) DIBAL / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 deg C

2: 65 percent / TiCl₄, Zn / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

With titanium tetrachloride; diisobutylaluminium hydride; triethylamine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)79046-0

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole (142075-81-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) LiNEt₂ / 1) THF, -78 deg C, 2) -78 deg C

2: 1) Et₃N, 2) DIBAL / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 deg C

3: 65 percent / TiCl₄, Zn / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

With lithium diethylamide; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)79046-0

upstream raw materials:

(2S,3S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanal

1,1-dibromomethane

t-butyldimethylsiyl triflate

3-(tert-butyldimethylsilanyloxy)propionaldehyde

Downstream raw materials:

4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-oxazole

C₂₄H₃₈NO₈PSi

[(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-(2-phenyl-oxazol-4-yl)-hept-6-enyl]-phosphonic acid dimethyl ester

C₂₇H₄₅NO₅Si₂