3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

Base Information

Chemical Name:3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone
CAS No.:138571-12-7
Molecular Formula:C₂₃H₂₄N₄O₅
Molecular Weight:436.467
Hs Code.:

Synonyms:3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

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Chemical Property of 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

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Technology Process of 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

There total 9 articles about 3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone 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:

: 4160-80-9
3-phenylglutaric acid anhydride

: 138571-12-7
3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / NaBH₄ / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 0.5 h

2: 100 percent / 2.5 M aq. NaOH

3: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

4: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

5: TsOH / benzene / 2 h / 120 °C

6: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

7: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

8: 1.) potassium hexamethyldisilazide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide, acetic acid / 1.) toluene, THF, -78 deg C, 0.5 h, 2.) toluene, THF, from -78 deg C to 35 deg C, 0.5 h

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; benzene;
DOI:10.1021/jm00083a006

Reference yield:

: 61198-49-0,61949-75-5,71302-21-1,25547-53-9
4-phenyltetrahydropyran-2-one

: 138571-12-7
3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / 2.5 M aq. NaOH

2: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

3: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

4: TsOH / benzene / 2 h / 120 °C

5: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

6: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

7: 1.) potassium hexamethyldisilazide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide, acetic acid / 1.) toluene, THF, -78 deg C, 0.5 h, 2.) toluene, THF, from -78 deg C to 35 deg C, 0.5 h

With sodium hydroxide; oxalyl dichloride; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; benzene;
DOI:10.1021/jm00083a006

Reference yield:

: 4165-96-2
3-phenylglutaric acid

: 138571-12-7
3-<4-(1,3-dioxolan-2-yl)-1-oxo-3(R)-phenyl-2(S)-azidobutyl>-4(S)-(phenylmethyl)-2-oxazolidinone

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 0 °C

2: 86 percent / NaBH₄ / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 0.5 h

3: 100 percent / 2.5 M aq. NaOH

4: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

5: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

6: TsOH / benzene / 2 h / 120 °C

7: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

8: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

9: 1.) potassium hexamethyldisilazide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide, acetic acid / 1.) toluene, THF, -78 deg C, 0.5 h, 2.) toluene, THF, from -78 deg C to 35 deg C, 0.5 h

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; benzene;
DOI:10.1021/jm00083a006