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

Base Information

• Chemical Name: (2S,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine
• CAS No.: 334976-45-3
• Molecular Formula: C₃₇H₄₅N₃O₅Si
• Molecular Weight: 639.867
• Mol file: 334976-45-3.mol

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

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

There total 8 articles about (2S,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-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: 83.0%

C29H40BrNO4Si (1174147-54-6) + 4-quinazolinol (491-36-1,134434-33-6) → (2S,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (334976-45-3)

Guidance literature:

With potassium hydroxide; In ethanol; Reflux;

DOI:10.1016/j.tetlet.2009.04.097

Reference yield: 78.0%

N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (334976-43-1) → (2S,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (334976-45-3) + (2R,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (334976-44-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ol015655z

Reference yield:

4-(tert-butyldiphenylsilyl)oxy-2-[(hydroxy)methyl]hexahydroisoxazolo[2,3-a]pyridine → (2S,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine (334976-45-3)

Guidance literature:

Multi-step reaction with 5 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

5.1: 22 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

With hydrogen; potassium hydride; sodium hydride; Dess-Martin periodane; triethylamine; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Dess-Martin oxidation;

DOI:10.1021/ol015655z

upstream raw materials:

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

4-Hydroxyquinazoline

di-tert-butyl dicarbonate

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