N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide

Base Information

Chemical Name:N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide
CAS No.:951385-81-2
Molecular Formula:C₂₆H₃₆ClNO₃Si
Molecular Weight:474.115
Hs Code.:

Synonyms:N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide

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Chemical Property of N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide

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Technology Process of N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide

There total 11 articles about N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide 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: 97.0%

: 951385-95-8
C₂₀H₂₂ClNO₃

: 18162-48-6
tert-butyldimethylsilyl chloride

: 951385-81-2
N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1021/ol701519b

Reference yield:

: 951385-89-0
(R,E)-N-(6-chloro-1-(4-methoxyphenyl)-3-oxohex-4-en-2-yl)benzamide

: 951385-81-2
N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide

Guidance literature:: Multi-step reaction with 4 steps

1: lithium tri-tert-butoxyaluminohydride / ethanol; tetrahydrofuran / 2 h / -78 °C

2: 83 percent / triphenyl phosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran; toluene / 0.25 h / 20 °C

3: 97 percent / aq. HCl / tetrahydrofuran; methanol / 12 h / 20 °C

4: 97 percent / imidazole / dimethylformamide / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium tri(t-butoxy)aluminum hydride; triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; 2: Mitsunobu reaction;
DOI:10.1021/ol701519b

Reference yield:

: 951385-88-9
(R)-N-(1-(methoxy(methyl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)benzamide

: 951385-81-2
N-((2R,3R,E)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: MeLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 86 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: lithium tri-tert-butoxyaluminohydride / ethanol; tetrahydrofuran / 2 h / -78 °C

3.1: 83 percent / triphenyl phosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran; toluene / 0.25 h / 20 °C

4.1: 97 percent / aq. HCl / tetrahydrofuran; methanol / 12 h / 20 °C

5.1: 97 percent / imidazole / dimethylformamide / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium tri(t-butoxy)aluminum hydride; methyllithium; triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; toluene; 3.1: Mitsunobu reaction;
DOI:10.1021/ol701519b