3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

Base Information

Chemical Name:3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester
CAS No.:946572-90-3
Molecular Formula:C₂₀H₃₂N₂O₆SSi
Molecular Weight:456.635
Hs Code.:

3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid <i>S</i>-(2-acetylamino-ethyl) ester

Synonyms:3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

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Chemical Property of 3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

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Technology Process of 3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

There total 13 articles about 3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-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:

: 946572-76-5
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid

: 1190-73-4
2-(acetylamino)ethanethiol

: 946572-90-3
3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

Guidance literature:: (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

2-(acetylamino)ethanethiol; With dmap; In N,N-dimethyl-formamide; for 40h;
DOI:10.1021/ja051430y

Reference yield:

: 3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid

: 1190-73-4
2-(acetylamino)ethanethiol

: 946572-90-3
3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

: 3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

Guidance literature:: 3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-propionic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

2-(acetylamino)ethanethiol; With dmap; In N,N-dimethyl-formamide; for 40h; Title compound not separated from byproducts;
DOI:10.1021/ja051430y

Reference yield:

: 864924-24-3
3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-benzaldehyde

: 946572-90-3
3-(tert-butyl-dimethyl-silanyloxy)-3-(3-hydroxy-5-nitro-phenyl)-2-methyl-thiopropionic acid S-(2-acetylamino-ethyl) ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Bu₂BOTf / diethyl ether; CH₂Cl₂ / 0.08 h / 0 °C

1.2: DIPEA / diethyl ether; CH₂Cl₂ / 0.75 h / 0 °C

1.3: diethyl ether; CH₂Cl₂ / 2 h / -78 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 16 h / 20 °C

3.1: H₂O₂; aq. LiOH / tetrahydrofuran / 16 h / 20 °C

4.1: 1,1'-carbonyldiimidazole / dimethylformamide / 3 h / 20 °C

4.2: DMAP / dimethylformamide / 40 h

With 2,6-dimethylpyridine; lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja051430y