tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether

Base Information

Chemical Name:tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether
CAS No.:347851-56-3
Molecular Formula:C₃₄H₄₃NO₄Si
Molecular Weight:557.805
Hs Code.:

Synonyms:tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether

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Chemical Property of tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether

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Technology Process of tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether

There total 6 articles about tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether 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: 56.0%

: 149524-96-9
2-(tert-butyldimethylsilanyloxymethyl)-3-phenylpropionaldehyde

: 347851-53-0
dimethyl [(3S)-4-phenyl-3-[(benzyloxycarbonyl)amino]-2-oxobutyl]phosphonate

: 347851-56-3
tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether

Guidance literature:: With potassium carbonate; In ethanol; for 24h;
DOI:10.1021/jo0016834

Reference yield:

: 35909-92-3
N-carbobenzoxy-L-phenylalanine methyl ester

: 347851-56-3
tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 100 percent / tetrahydrofuran; hexane

2.1: 56 percent / K₂CO₃ / ethanol / 24 h

With n-butyllithium; potassium carbonate; In tetrahydrofuran; ethanol; hexane; 2.1: Wadsworth-Emmons reaction;
DOI:10.1021/jo0016834

Reference yield:

: 85677-12-9
2-benzyl-3-hydroxypropionic acid methyl ester

: 347851-56-3
tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / imidazole / 0.5 h

2: 87 percent / DIBALH / toluene / 1.5 h / -90 - -80 °C

3: 56 percent / K₂CO₃ / ethanol / 24 h

With 1H-imidazole; diisobutylaluminium hydride; potassium carbonate; In ethanol; toluene; 3: Wadsworth-Emmons reaction;
DOI:10.1021/jo0016834