(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one

Base Information

Chemical Name:(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one
CAS No.:768391-60-2
Molecular Formula:C₂₈H₂₈N₂O₇
Molecular Weight:504.54
Hs Code.:

Synonyms:(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one

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Chemical Property of (2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one

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Technology Process of (2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one

There total 1 articles about (2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-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: 82.0%

: 555-16-8
4-nitrobenzaldehdye

: 496877-70-4
(S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one

: (4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one

: 768391-60-2
(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one

Guidance literature:: With triethyl borane; trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; at -78 - 0 ℃; for 1.5h;
DOI:10.1016/j.tet.2004.05.123

Reference yield: 88.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 768391-60-2
(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one

: 768392-05-8
(2'S,3'R,4S)-4-benzyl-3-[2'-benzyloxy-3'-(tert-butyldimethylsilanyloxy)-3'-(4''-nitrophenyl)propionyl]-5,5-dimethyloxazolidin-2-one

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1016/j.tet.2004.05.123

Reference yield:

: 768391-60-2
(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one

: (2S,3R)-2-benzyloxy-3-(tert-butyldimethylsilanoxy)-3-(4'-nitrophenyl)propionaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / imidazole; DMAP / dimethylformamide / 18 h / 20 °C

2: 99 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

3: 76 percent / aq. K₂CO₃ / methanol / 0.25 h / 20 °C

With 1H-imidazole; dmap; diisobutylaluminium hydride; potassium carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.05.123