methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate

Base Information

• Chemical Name: methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate
• CAS No.: 219507-06-9
• Molecular Formula: C₂₈H₃₄N₄O₁₀S
• Molecular Weight: 618.665

Synonyms:methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate

Chemical Property of methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate

There total 8 articles about methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate 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: 100.0%

(S)-4-[(S)-2-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-butane-1-sulfinyl]-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester (219507-03-6) → methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate (219507-06-9)

Guidance literature:

With mesitylenesulfonylhydroxylamine; In acetonitrile; Ambient temperature;

DOI:10.1016/S0968-0896(98)00142-4

Reference yield:

(4R,5S)-(+)-4-methyl-3-(1'-oxobutyl)-5-phenyloxazolidin-2-one (80697-91-2) → methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate (219507-06-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -15 deg C, 2.) CH₂Cl₂, -78 deg C to 0 deg C

2: 100 percent / Et₃N / CH₂Cl₂

3: 84 percent / NaI / acetone / Heating

4: 100 percent / K₂CO₃ / dimethylformamide / 1 h / 60 °C

5: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 24 h / 25 °C

6: 100 percent / O-mesitylenesulfonylhydroxylamine / acetonitrile / Ambient temperature

With sodium periodate; di-n-butylboryl trifluoromethanesulfonate; mesitylenesulfonylhydroxylamine; potassium carbonate; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0968-0896(98)00142-4

Reference yield:

(4R,5S)-3-((S)-2-Iodomethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one (219506-97-5) → methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate (219507-06-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / K₂CO₃ / dimethylformamide / 1 h / 60 °C

2: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 24 h / 25 °C

3: 100 percent / O-mesitylenesulfonylhydroxylamine / acetonitrile / Ambient temperature

With sodium periodate; mesitylenesulfonylhydroxylamine; potassium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(98)00142-4

upstream raw materials:

(S)-4-[(S)-2-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-butane-1-sulfinyl]-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester

(4R,5S)-(+)-4-methyl-3-(1'-oxobutyl)-5-phenyloxazolidin-2-one

(4R,5S)-3-((S)-2-Iodomethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one

(4R,5S)-3-((R)-2-Hydroxymethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one

Downstream raw materials:

(S)-4-((1R,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ⁶-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester

(S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ⁶-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester

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