(R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one

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Chemical Name:(R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one
CAS No.:864924-25-4
Molecular Formula:C₂₆H₃₄N₂O₇Si
Molecular Weight:514.651
Hs Code.:

Synonyms:(R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one

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Chemical Property of (R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one

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Technology Process of (R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one

There total 7 articles about (R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one 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:

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

: 101711-78-8,131685-53-5
(3R)-3-propionyl-4-benzyloxazolidin-2-one

: 864924-25-4
(R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one

Guidance literature:: (3R)-3-propionyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; In diethyl ether; dichloromethane; for 0.0833333h; cooling;

With N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; at 0 ℃; for 0.75h;

3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-benzaldehyde; In diethyl ether; dichloromethane; at -78 - 0 ℃; for 3h;
DOI:10.1021/ja051430y

Reference yield:

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

: 101711-78-8,131685-53-5
(3R)-3-propionyl-4-benzyloxazolidin-2-one

: 864924-25-4
(R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one

: (R)-4-Benzyl-3-{(2S,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one

Guidance literature:: (3R)-3-propionyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 0 ℃; for 0.0833333h;

With N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; at 0 ℃; for 0.75h;

3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-benzaldehyde; In diethyl ether; dichloromethane; at -78 ℃; for 2h; Title compound not separated from byproducts;
DOI:10.1021/ja051430y

Reference yield:

: 99-34-3
3,5-dinitrobenzoic acid

: 864924-25-4
(R)-4-Benzyl-3-{(2R,3R)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-nitro-phenyl]-3-hydroxy-2-methyl-propionyl}-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / hexamethylphosphoric acid triamide / 20 h / 85 °C

2.1: 95 percent / AcOH; HBr / 20 h / Heating

3.1: 79 percent / NaBH₄; I₂ / tetrahydrofuran / 6 h / 20 °C

4.1: 75 percent / MnO₂ / CH₂Cl₂; acetone / 24 h / 20 °C

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

6.1: Bu₂BOTf / diethyl ether; CH₂Cl₂ / 0.08 h / cooling

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

6.3: diethyl ether; CH₂Cl₂ / 3 h / -78 - 0 °C

With 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; hydrogen bromide; iodine; acetic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja051430y