2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide

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Chemical Name:2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide
CAS No.:939054-93-0
Molecular Formula:C₃₈H₄₈N₂O₅Si
Molecular Weight:640.895
Hs Code.:

Synonyms:2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide

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Chemical Property of 2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide

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Technology Process of 2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide

There total 12 articles about 2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide 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: 87.0%

: 939054-88-3
2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-oxo-1,2,3,6-tetrahydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide

: 420-37-1
trimethoxonium tetrafluoroborate

: 939054-93-0
2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide

Guidance literature:: With caesium carbonate; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/jo070144x

Reference yield:

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

: 939054-93-0
2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide

Guidance literature:: Multi-step reaction with 10 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

5.1: 80 percent / NaHMDS / tetrahydrofuran / 3 h / -78 °C

6.1: 89 percent / tetrahydrofuran; methanol / 0.5 h / 20 °C

7.1: 82 percent / DBU / acetonitrile / 1 h / Heating

8.1: 92 percent / K₂CO₃; thiophenol / dimethylformamide / 1 h / 20 °C

9.1: 96 percent / AlMe₃ / CH₂Cl₂; hexane / 48 h / 20 °C

10.1: 87 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

With triethylsilane; dmap; barium dihydroxide; trimethylaluminum; sodium hexamethyldisilazane; potassium carbonate; caesium carbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 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

: 939054-93-0
2-{(3R)-3-[(3E)-6-(tert-butyldiphenylsilanyloxy)hex-3-enyl]-2-methoxy-3,6-dihydropyridin-3-yl}-N-(3,4-dimethoxyphenyl)acetamide

Guidance literature:: Multi-step reaction with 9 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

4.1: 80 percent / NaHMDS / tetrahydrofuran / 3 h / -78 °C

5.1: 89 percent / tetrahydrofuran; methanol / 0.5 h / 20 °C

6.1: 82 percent / DBU / acetonitrile / 1 h / Heating

7.1: 92 percent / K₂CO₃; thiophenol / dimethylformamide / 1 h / 20 °C

8.1: 96 percent / AlMe₃ / CH₂Cl₂; hexane / 48 h / 20 °C

9.1: 87 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

With triethylsilane; dmap; trimethylaluminum; sodium hexamethyldisilazane; potassium carbonate; caesium carbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3.2: aza-Claisen rearrangement;
DOI:10.1021/jo070144x