N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-4-en-2-yl]benzamide

Base Information

Chemical Name:N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-4-en-2-yl]benzamide
CAS No.:938449-08-2
Molecular Formula:C₂₅H₄₀ClNO₂Si
Molecular Weight:450.137
Hs Code.:

Synonyms:N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-4-en-2-yl]benzamide

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Chemical Property of N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-4-en-2-yl]benzamide

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Technology Process of N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-4-en-2-yl]benzamide

There total 5 articles about N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-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: 96.0%

: 938449-04-8
N-[(E,2S,3S)-6-chloro-1-cyclohexyl-3-hydroxyhex-4-en-2-yl]benzamide

: 18162-48-6
tert-butyldimethylsilyl chloride

: 938449-08-2
N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-4-en-2-yl]benzamide

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1002/ejoc.200600927

Reference yield:

: 938448-92-1
methyl (E)-3-[(4S,5S)-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazol-5-yl]acrylate

: 938449-08-2
N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-4-en-2-yl]benzamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / i-Bu₂AlH / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: 91 percent / p-toluenesulfonyl chloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

3.1: aq. HCl / tetrahydrofuran; methanol / 12 h / 20 °C

3.2: 85 percent / aq. sodium hydrogencarbonate / tetrahydrofuran; methanol / 3 h / 20 °C / pH 9.0

4.1: 96 percent / imidazole / dimethylformamide / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; diisobutylaluminium hydride; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200600927

Reference yield:

: 938448-96-5
(E)-3-[(4S,5S)-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazol-5-yl]prop-2-en-1-ol

: 938449-08-2
N-[(E,2S,3S)-3-(tert-butyldimethylsilyloxy)-6-chloro-1-cyclohexylhex-4-en-2-yl]benzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 91 percent / p-toluenesulfonyl chloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2.1: aq. HCl / tetrahydrofuran; methanol / 12 h / 20 °C

2.2: 85 percent / aq. sodium hydrogencarbonate / tetrahydrofuran; methanol / 3 h / 20 °C / pH 9.0

3.1: 96 percent / imidazole / dimethylformamide / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200600927