(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole

Base Information

• Chemical Name: (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole
• CAS No.: 157117-23-2
• Molecular Formula: C₄₁H₅₇NO₃Si
• Molecular Weight: 639.994
• Mol file: 157117-23-2.mol

Synonyms:(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole

Chemical Property of (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole

There total 9 articles about (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-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: 84.0%

laurylmagnesium bromide (15890-72-9) + Toluene-4-sulfonic acid (2S,3S)-3-[(4S,5S)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-oxiranylmethyl ester (157117-22-1) → (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole (157117-23-2)

Guidance literature:

With copper(I) bromide; In tetrahydrofuran; at -30 - 0 ℃; for 4h;

DOI:10.1016/S0040-4039(00)75806-0

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole (157117-23-2)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine; CH₂Cl₂ / 24 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: Et₃N / pyridine; toluene / 24 h / 110 °C

4: TiCl₄, PhSH / CH₂Cl₂ / 2 h / 0 °C

5: K₂CO₃ / methanol / 2 h / 0 °C

6: Et₃N / 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

7: 84 percent / CuBr / tetrahydrofuran / 4 h / -30 - 0 °C

With titanium tetrachloride; potassium carbonate; thiophenol; triethylamine; copper(I) bromide; dmap; In tetrahydrofuran; pyridine; methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)75806-0

Reference yield:

4,6-O-ethylidene-N-benzoyl-D-glucosamine → (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole (157117-23-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / NaBH₄ / propan-2-ol; H₂O / 1 h / 0 °C

2: pyridine; CH₂Cl₂ / 24 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: Et₃N / pyridine; toluene / 24 h / 110 °C

5: TiCl₄, PhSH / CH₂Cl₂ / 2 h / 0 °C

6: K₂CO₃ / methanol / 2 h / 0 °C

7: Et₃N / 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

8: 84 percent / CuBr / tetrahydrofuran / 4 h / -30 - 0 °C

With sodium tetrahydroborate; titanium tetrachloride; potassium carbonate; thiophenol; triethylamine; copper(I) bromide; dmap; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; isopropyl alcohol; toluene;

DOI:10.1016/S0040-4039(00)75806-0

upstream raw materials:

laurylmagnesium bromide

Toluene-4-sulfonic acid (2S,3S)-3-[(4S,5S)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-oxiranylmethyl ester

tert-butylchlorodiphenylsilane

2-Benzamido-2-deoxy-4,6-O-ethylidene-D-glucitol

Downstream raw materials:

D-ribo-phytosphingosine

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

N-[(E)-(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-heptadec-3-enyl]-benzamide

N-[(1S,2S,3R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2,3-dihydroxy-heptadecyl]-benzamide