3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne

Base Information

• Chemical Name: 3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne
• CAS No.: 875439-71-7
• Molecular Formula: C₃₃H₄₃NO₃Si₂
• Molecular Weight: 557.88
• Mol file: 875439-71-7.mol

Synonyms:3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne

Chemical Property of 3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne

There total 1 articles about 3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne 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: 96.0%

3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzyl bromide (875439-61-5) + tris(2-(trimethylsilyl)ethynyl)indium (250643-77-7) → 3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne (875439-71-7)

Guidance literature:

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 65 ℃; for 3h;

DOI:10.1021/ol052588q DOI:10.1021/ol0702270

Reference yield:

3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne (875439-71-7) → 3-(tert-butyl-diphenyl-silanyloxy)-5-(2-methyl-penta-2,4-dienyl)-phenylamine (936824-92-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / -20 - 0 °C

2.1: Cp₂ZrCl₂ / hexane; 1,2-dichloro-ethane / 0.83 h / 0 - 20 °C

2.2: 1,2-dichloro-ethane; hexane / 72 h / 20 °C

2.3: 58 percent / iodine / 1,2-dichloro-ethane; hexane; tetrahydrofuran / -30 - 0 °C

3.1: 89 percent / pyridine / CH₂Cl₂ / 3 h / 0 °C

4.1: 79 percent / Pd(PPh₃)4 / dimethylformamide / 4 h / 55 °C

5.1: 48 percent / anhydrous ZnCl₂ / nitromethane / 1 h / sonication

6.1: 89 percent / imidazole; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; 1H-imidazole; dmap; zirconocene dichloride; tetrabutyl ammonium fluoride; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; nitromethane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 4.1: Stille coupling;

DOI:10.1021/ol0702270

Reference yield:

3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne (875439-71-7) → C53H80O6Si3IN

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / -20 - 0 °C

2.1: Cp₂ZrCl₂ / hexane; 1,2-dichloro-ethane / 0.83 h / 0 - 20 °C

2.2: 1,2-dichloro-ethane; hexane / 72 h / 20 °C

2.3: 58 percent / iodine / 1,2-dichloro-ethane; hexane; tetrahydrofuran / -30 - 0 °C

3.1: 94 percent / imidazole; DMAP / CH₂Cl₂ / 1.5 h

4.1: 70 percent / N,N-bis(2-oxo-3-oxazolidinyl)phosphonic acid chloride; DIEA / CH₂Cl₂ / 18 h / 20 °C

5.1: K₂CO₃; Bu₄NCl; NEt₃ / Pd(OAc)2 / dimethylformamide / 20 °C

With 1H-imidazole; dmap; zirconocene dichloride; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium diacetate; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0702270

upstream raw materials:

3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzyl bromide

tris(2-(trimethylsilyl)ethynyl)indium

Downstream raw materials:

3-amino-5-[(E)-3-iodo-2-methylprop-2-enyl]-phenol

N,O-bis(2-trimethylsilylethoxycarbonyl)-3-amino-5-[(E)-3-iodo-2-methylallyl]-phenol

N,O-bis(2-trimethylsilylethoxycarbonyl)-3-amino-5-(2-methyl-penta-2,4-dienyl)-phenol

3-(tert-butyl-diphenyl-silanyloxy)-5-(2-methyl-penta-2,4-dienyl)-phenylamine