(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol

Base Information

Chemical Name:(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol
CAS No.:347851-57-4
Molecular Formula:C₂₈H₂₉NO₄
Molecular Weight:443.543
Hs Code.:

Synonyms:(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol

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Chemical Property of (2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol

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Technology Process of (2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol

There total 7 articles about (2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol 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: 46.0%

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

: 347851-57-4
(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol

Guidance literature:: With acetic acid; In tetrahydrofuran; water; for 72h;
DOI:10.1021/jo0016834

Reference yield:

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

: 347851-57-4
(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol

Guidance literature:: Multi-step reaction with 3 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

3.1: 46 percent / AcOH / tetrahydrofuran; H₂O / 72 h

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

Reference yield:

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

: 347851-57-4
(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-hepten-1-ol

Guidance literature:: Multi-step reaction with 4 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

4: 46 percent / AcOH / tetrahydrofuran; H₂O / 72 h

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