N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine
• CAS No.: 334976-43-1
• Molecular Formula: C₃₇H₄₇N₃O₅Si
• Molecular Weight: 641.883
• Mol file: 334976-43-1.mol

Synonyms:N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

Chemical Property of N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

There total 5 articles about N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine 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: 77.0%

4-Hydroxyquinazoline (491-36-1) + N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[(oxiranyl)methyl]piperidine (334976-42-0) → N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (334976-43-1)

Guidance literature:

4-Hydroxyquinazoline; With potassium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[(oxiranyl)methyl]piperidine; In N,N-dimethyl-formamide; at 70 ℃; for 40h; Further stages.;

DOI:10.1021/ol015655z

Reference yield:

4-(tert-butyldiphenylsilyl)oxy-2-[(hydroxy)methyl]hexahydroisoxazolo[2,3-a]pyridine → N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (334976-43-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂ / PdCl₂ / methanol / 12 h / 20 °C

2.1: Et₃N / CH₂Cl₂ / 10 h / 20 °C

3.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

3.2: 92 percent / N-tosylimidazole / tetrahydrofuran / 12 h / 20 °C

4.1: KH / dimethylformamide / 0.5 h / 0 °C

4.2: 77 percent / dimethylformamide / 40 h / 70 °C

With hydrogen; potassium hydride; sodium hydride; triethylamine; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol015655z

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (334976-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / CH₂Cl₂ / 10 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

2.2: 92 percent / N-tosylimidazole / tetrahydrofuran / 12 h / 20 °C

3.1: KH / dimethylformamide / 0.5 h / 0 °C

3.2: 77 percent / dimethylformamide / 40 h / 70 °C

With potassium hydride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol015655z

upstream raw materials:

4-Hydroxyquinazoline

N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[(oxiranyl)methyl]piperidine

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-(2,3-dihydroxypropyl)piperidine

Downstream raw materials:

(2S,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

(2R,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine