(4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester

Base Information

Chemical Name:(4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester
CAS No.:939054-90-7
Molecular Formula:C₃₀H₃₉NO₄Si
Molecular Weight:505.729
Hs Code.:

Synonyms:(4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester

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Chemical Property of (4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester

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Technology Process of (4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester

There total 5 articles about (4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester 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: 55.0%

: 939054-96-3
(5E)-2-((2R,E)-1-acetylaziridin-2-ylmethylene)-8-(tert-butyldiphenylsilanyloxy)oct-5-enoic acid methyl ester

: 939054-90-7
(4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester

Guidance literature:: (5E)-2-((2R,E)-1-acetylaziridin-2-ylmethylene)-8-(tert-butyldiphenylsilanyloxy)oct-5-enoic acid methyl ester; With lithium hexamethyldisilazane; In hexane; toluene; at -78 ℃; for 0.333333h;

In hexane; toluene; for 0.166667h; Further stages.; Heating;
DOI:10.1021/jo070144x

Reference yield:

: 939054-89-4
(5E)-8-(tert-butyldiphenylsilanyloxy)-2-(diethoxyphosphoryl)oct-5-enoic acid methyl ester

: 939054-90-7
(4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / Ba(OH)2 / tetrahydrofuran; H₂O / 5 h / 20 °C

2.1: 86 percent / Et₃SiH; trifluoroacetic acid / CH₂Cl₂ / 0.33 h / 0 °C

3.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 0.08 h / 0 °C

4.1: LHMDS / toluene; hexane / 0.33 h / -78 °C

4.2: 55 percent / toluene; hexane / 0.17 h / Heating

With triethylsilane; dmap; barium dihydroxide; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.1: Horner-Wadsworth-Emmons reaction / 4.2: aza-Claisen rearrangement;
DOI:10.1021/jo070144x

Reference yield:

: 939054-94-1
(5E)-8-(tert-butyldiphenylsilanyloxy)-2-((2R,E)-1-tritylaziridin-2-ylmethylene)oct-5-enoic acid methyl ester

: 939054-90-7
(4R)-4-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / Et₃SiH; trifluoroacetic acid / CH₂Cl₂ / 0.33 h / 0 °C

2.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 0.08 h / 0 °C

3.1: LHMDS / toluene; hexane / 0.33 h / -78 °C

3.2: 55 percent / toluene; hexane / 0.17 h / Heating

With triethylsilane; dmap; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In hexane; dichloromethane; toluene; 3.2: aza-Claisen rearrangement;
DOI:10.1021/jo070144x