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

Base Information

Chemical Name:(2R,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine
CAS No.:334976-44-2
Molecular Formula:C₃₇H₄₅N₃O₅Si
Molecular Weight:639.867
Hs Code.:

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

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

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

There total 7 articles about (2R,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: 78.0%

: 334976-43-1
N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

: 334976-45-3
(2S,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

: 334976-44-2
(2R,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

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

: 334976-44-2
(2R,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

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: 78 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

Reference yield:

: 491-36-1
4-Hydroxyquinazoline

: 334976-44-2
(2R,3S)-N-(tert-butoxycarbonyl)-3-(tert-butyldiphenylsilyl)oxy-2-[2-oxo-3-(4-oxo-4H-quinazolin-3-yl)propyl]piperidine

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 77 percent / dimethylformamide / 40 h / 70 °C

2.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

With potassium hydride; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide; 2.1: Dess-Martin oxidation;
DOI:10.1021/ol015655z