(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

Base Information

Chemical Name:(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester
CAS No.:930579-51-4
Molecular Formula:C₂₄H₃₉NO₆Si
Molecular Weight:465.662
Hs Code.:

Synonyms:(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

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Chemical Property of (2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

Chemical Property:

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Technology Process of (2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

There total 8 articles about (2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl 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:

: (2S,3S)-3-Benzylamino-2-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

: 36239-09-5
ethyl chlorocarbonylacetate

: 930579-51-4
(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;
DOI:10.1021/jo0606002

Reference yield:

: 898831-82-8
(2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

: 930579-51-4
(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: cesium carbonate; thiophenol / acetonitrile / 12 h / 20 °C

2: 2.87 g / diisopropylethylamine / CH₂Cl₂ / 10 h / 20 °C

With caesium carbonate; thiophenol; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2006.12.055

Reference yield:

: 159721-18-3
(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester

: 930579-51-4
(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: DIBAL-H / toluene; CH₂Cl₂ / 0.5 h / -78 °C

1.2: ZnCl₂; LiCl / tetrahydrofuran / 0.5 h / 0 °C

1.3: 88 percent / CH₂Cl₂; toluene; tetrahydrofuran / 2 h / 0 °C

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

3.1: O₃ / ethyl acetate / 1.33 h / -78 °C

3.2: Me₂S / ethyl acetate / -78 - 0 °C

4.1: 2-methyl-2-butene; NaH₂PO₄*2H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 15 h / 20 °C

5.1: SOCl₂ / 1 h / Heating

6.1: 87.1 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

7.1: LiOH*2H₂O; mercaptoacetic acid / dimethylformamide / 4 h

8.1: (i-Pr)2NEt / CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; diisobutylaluminium hydride; ozone; mercaptoacetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo0606002