ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-enoate

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Chemical Name:ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-enoate
CAS No.:676460-55-2
Molecular Formula:C₂₀H₂₈FNO₅
Molecular Weight:381.444
Hs Code.:

Synonyms:ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-enoate

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Chemical Property of ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-enoate

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Technology Process of ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-enoate

There total 6 articles about ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-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: 65.0%

: 110-88-3
1,3,5-Trioxan

: 676460-48-3
ethyl (5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate

: 676460-55-2
ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-enoate

Guidance literature:: 1,3,5-Trioxan; With (1,1';3',1''-terphenyl)-2'-ol; trimethylaluminum; In hexane; dichloromethane; at 0 ℃; for 1h;

ethyl (5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4,4-difluoro-6-phenylhex-2-enoate; With samarium diiodide; In tetrahydrofuran; ethanol; hexane; at 0 ℃; for 1h;
DOI:10.1021/jo035709d

Reference yield:

: 122-78-1
phenylacetaldehyde

: 676460-55-2
ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 0 °C

2.1: 490 mg / Et₂Zn / RhCl(PPh₃)3 / tetrahydrofuran; hexane / 0.5 h / 0 °C

3.1: H₂ / (Pd(OH)2/C / ethanol / 20 °C

3.2: 51 percent / tetrahydrofuran / Heating

4.1: DIBALH / CH₂Cl₂; toluene / -78 °C

5.1: LiCl; iPr₂NEt / acetonitrile / 0.33 h / 0 °C

5.2: 2.5 g / acetonitrile / 20 °C

6.1: 2,6-diphenylphenol; Me₃Al / CH₂Cl₂; hexane / 1 h / 0 °C

6.2: 65 percent / SmI₂ / ethanol; hexane; tetrahydrofuran / 1 h / 0 °C

With (1,1';3',1''-terphenyl)-2'-ol; hydrogen; trimethylaluminum; diethylzinc; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium hydroxide - carbon; RhCl(PPh₃)3; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; acetonitrile; 5.2: Horner-Emmons olefination;
DOI:10.1021/jo035709d

Reference yield:

: ((R)-2-Methoxy-1-phenyl-ethyl)-[2-phenyl-eth-(E)-ylidene]-amine

: 676460-55-2
ethyl (5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-4-fluoro-2-hydroxymethyl-6-phenylhex-3-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 490 mg / Et₂Zn / RhCl(PPh₃)3 / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.1: H₂ / (Pd(OH)2/C / ethanol / 20 °C

2.2: 51 percent / tetrahydrofuran / Heating

3.1: DIBALH / CH₂Cl₂; toluene / -78 °C

4.1: LiCl; iPr₂NEt / acetonitrile / 0.33 h / 0 °C

4.2: 2.5 g / acetonitrile / 20 °C

5.1: 2,6-diphenylphenol; Me₃Al / CH₂Cl₂; hexane / 1 h / 0 °C

5.2: 65 percent / SmI₂ / ethanol; hexane; tetrahydrofuran / 1 h / 0 °C

With (1,1';3',1''-terphenyl)-2'-ol; hydrogen; trimethylaluminum; diethylzinc; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium hydroxide - carbon; RhCl(PPh₃)3; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; acetonitrile; 4.2: Horner-Emmons olefination;
DOI:10.1021/jo035709d