tert-butyl (5R,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate

Base Information

Chemical Name:tert-butyl (5R,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate
CAS No.:896506-22-2
Molecular Formula:C₂₁H₂₉F₂NO₄
Molecular Weight:397.462
Hs Code.:

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

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

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

There total 2 articles about tert-butyl (5R,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-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: 61.1%

: (o-MePhO₂)2P(O)CH₂CO₂t-Bu

: (1-benzyl-2,2-difluoro-3-oxo-propyl)-carbamic acid tert-butyl ester

: 896506-22-2
tert-butyl (5R,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate

: tert-butyl (5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate

Guidance literature:: (o-MePhO₂)2P(O)CH₂CO₂t-Bu; With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In tetrahydrofuran; for 0.166667h;

(1-benzyl-2,2-difluoro-3-oxo-propyl)-carbamic acid tert-butyl ester; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/jo060202z

Reference yield:

: 676460-46-1
ethyl (3R)-3-[(tert-butoxycarbonyl)amino]-2,2-difluoro-4-phenylbutanoate

: 896506-22-2
tert-butyl (5R,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

2.1: NaI; DBU / tetrahydrofuran / 0.17 h

2.2: 61.1 percent / tetrahydrofuran / 2 h / 0 °C

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In tetrahydrofuran; dichloromethane; toluene; 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo060202z

Reference yield:

: 896506-22-2
tert-butyl (5R,2Z)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate

: (3R,6R)-6-benzyl-3,6-dihydro-5-fluoro-1,3-dimethylpyridin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: HCl / dioxane / 1 h / 20 °C

2.1: 73 percent / (i-Pr)2NEt; HOAt; 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide / 23 h / 20 °C

3.1: 84 percent / NaH / tetrahydrofuran; various solvent(s) / 2 h / 20 °C

4.1: Me₃CuLi₂*LiI*3LiBr / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C

4.2: 76.8 percent / H₂O / tetrahydrofuran; diethyl ether

5.1: LDA / tetrahydrofuran

5.2: tetrahydrofuran

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; Me₃CuLi₂*LiI*3LiBr; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo060202z