t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate

Base Information

Chemical Name:t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate
CAS No.:894407-11-5
Molecular Formula:C₂₂H₃₃NO₄
Molecular Weight:375.508
Hs Code.:

Synonyms:t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate

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Chemical Property of t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate

Chemical Property:

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Technology Process of t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate

There total 4 articles about t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate 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:

: tert-butyl (2S,3S)-3-formyl-1-phenylbutan-2-ylcarbamate

: (o-MePhO₂)2P(O)CH₂CO₂t-Bu

: 894407-11-5
t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In tetrahydrofuran;
DOI:10.1016/j.tetlet.2005.04.057

Reference yield:

: 289493-08-9
methyl (2S,3S)-3-[N-(tert-butoxycarbonyl)amino]-2-methyl-4-phenylbutanoate

: 894407-11-5
t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: DIBALH / CH₂Cl₂; toluene / 0.5 h / -78 °C

2: 6.4 mg / NaI; DBU / tetrahydrofuran / 4 h / 0 °C

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In tetrahydrofuran; dichloromethane; toluene; 2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo060390t

Reference yield:

: 51871-62-6
(S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid

: 894407-11-5
t-butyl (4S,5S,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4-methyl-6-phenylhex-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: 89.3 percent / KHCO₃ / dimethylformamide / 12 h

2: 50.1 percent / iPr₂NH; nBuLi / tetrahydrofuran; hexane / 3 h / -78 - 0 °C

3: DIBALH / CH₂Cl₂; toluene / 0.5 h / -78 °C

4: 6.4 mg / NaI; DBU / tetrahydrofuran / 4 h / 0 °C

With n-butyllithium; diisobutylaluminium hydride; potassium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; sodium iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo060390t