(2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric acid methyl ester

Base Information

Chemical Name:(2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric acid methyl ester
CAS No.:902468-37-5
Molecular Formula:C₃₂H₄₄N₂O₇Si
Molecular Weight:596.796
Hs Code.:

Synonyms:(2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric acid methyl ester

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Chemical Property of (2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric acid methyl ester

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Technology Process of (2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric acid methyl ester

There total 6 articles about (2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric 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: 90.0%

: 902468-36-4
(2S)-[bis(tert-butyloxycarbonyl)amino]-4-cyano-4-hydroxybutyric acid methyl ester

: 58479-61-1
tert-butylchlorodiphenylsilane

: 902468-37-5
(2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric acid methyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 15h;
DOI:10.1002/chem.200501128

Reference yield:

: 40856-59-5,132957-40-5
tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate

: 902468-37-5
(2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / N,N-dimethylaminopyridine / acetonitrile / 15 h / 20 °C

2.1: aq. CsOH / methanol / 2 h / 20 °C

2.2: 79 percent / dimethylformamide / 18 h / 20 °C

3.1: DMSO; oxalyl chloride; NEtiPr₂ / CH₂Cl₂ / -60 - 20 °C

4.1: CH₂Cl₂ / 20 h / 20 °C

5.1: 11.68 g / ammonium fluoride / methanol / 0.08 h

6.1: 90 percent / imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; dmap; cesium hydroxide; ammonium fluoride; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Swern oxidation;
DOI:10.1002/chem.200501128

Reference yield:

: 902468-35-3
(2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}butyrolactone

: 902468-37-5
(2S)-[bis(tert-butyloxycarbonyl)amino]-4-(tert-butyldiphenylsilanyloxy)-4-cyanobutyric acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: aq. CsOH / methanol / 2 h / 20 °C

1.2: 79 percent / dimethylformamide / 18 h / 20 °C

2.1: DMSO; oxalyl chloride; NEtiPr₂ / CH₂Cl₂ / -60 - 20 °C

3.1: CH₂Cl₂ / 20 h / 20 °C

4.1: 11.68 g / ammonium fluoride / methanol / 0.08 h

5.1: 90 percent / imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; cesium hydroxide; ammonium fluoride; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Swern oxidation;
DOI:10.1002/chem.200501128