benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate

Base Information

Chemical Name:benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate
CAS No.:865704-55-8
Molecular Formula:C₂₇H₃₂N₂O₇
Molecular Weight:496.56
Hs Code.:

Synonyms:benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate

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Chemical Property of benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate

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Technology Process of benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate

There total 8 articles about benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate 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:

: 865704-45-6
4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid

: 865704-55-8
benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 50 percent / P₂O₅ / CHCl₃ / 60 h / 20 °C

2.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

3.1: 98 percent / TFA / CH₂Cl₂ / 20 °C

4.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

5.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

6.1: toluene / Heating

7.1: 0.91 g / toluene / Heating

With sodium azide; sodium hexamethyldisilazane; phosphorus pentoxide; triethylamine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; chloroform; toluene; 6.1: Curtius rearrangement;
DOI:10.1055/s-2005-865362

Reference yield:

: 865704-46-7
tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate

: 865704-55-8
benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

2.1: 98 percent / TFA / CH₂Cl₂ / 20 °C

3.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

4.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

5.1: toluene / Heating

6.1: 0.91 g / toluene / Heating

With sodium azide; sodium hexamethyldisilazane; triethylamine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; toluene; 5.1: Curtius rearrangement;
DOI:10.1055/s-2005-865362

Reference yield:

: 865704-51-4
(3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-5-(benzyloxy)-5-oxopentanoic acid

: 865704-55-8
benzyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoate

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

2: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

3: toluene / Heating

4: 0.91 g / toluene / Heating

With sodium azide; triethylamine; In tetrahydrofuran; toluene; 3: Curtius rearrangement;
DOI:10.1055/s-2005-865362