(4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one
• CAS No.: 1312443-45-0
• Molecular Formula: C₁₉H₂₂N₂O₃
• Molecular Weight: 326.395

Synonyms:(4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one

Chemical Property of (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one

There total 4 articles about (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-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:

carbon monoxide (201230-82-2) + (2R,3S,4S,5R)-2,5-diamino-1,6-diphenyl-3,4-hexanediol (219586-75-1) → (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one (1312443-45-0) + (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one (153223-11-1) + (4R,4'R,5S,5'S)-4,4'-dibenzyl-[5,5'-bioxazolidine]-2,2'-dione

Guidance literature:

With pyridine; tungsten hexacarbonyl; iodine; In 1,2-dichloro-ethane; at 80 ℃; for 16h; under 60006 Torr; Autoclave;

DOI:10.1016/j.tet.2011.04.015

Reference yield:

N-(benzyloxycarbonyl)-D-phenylalaninol (58917-85-4) → (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one (1312443-45-0) + (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one (153223-11-1) + (4R,4'R,5S,5'S)-4,4'-dibenzyl-[5,5'-bioxazolidine]-2,2'-dione

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.17 h / -78 °C / Inert atmosphere

1.2: 2.25 h / -78 °C / Inert atmosphere

2.1: Vanadium (III) chloride-(tris-tetrahydrofuran); zinc / dichloromethane / 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; ammonium formate / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere

4.1: pyridine; tungsten hexacarbonyl; iodine / 1,2-dichloro-ethane / 16 h / 80 °C / 60006 Torr / Autoclave

With pyridine; oxalyl dichloride; Vanadium (III) chloride-(tris-tetrahydrofuran); tungsten hexacarbonyl; palladium 10% on activated carbon; iodine; ammonium formate; dimethyl sulfoxide; zinc; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 1.2: Swern oxidation;

DOI:10.1016/j.tet.2011.04.015

Reference yield:

N-(benzyloxycarbonyl)-D-phenylalaninal (63219-70-5) → (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one (1312443-45-0) + (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one (153223-11-1) + (4R,4'R,5S,5'S)-4,4'-dibenzyl-[5,5'-bioxazolidine]-2,2'-dione

Guidance literature:

Multi-step reaction with 3 steps

1: Vanadium (III) chloride-(tris-tetrahydrofuran); zinc / dichloromethane / 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; ammonium formate / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere

3: pyridine; tungsten hexacarbonyl; iodine / 1,2-dichloro-ethane / 16 h / 80 °C / 60006 Torr / Autoclave

With pyridine; Vanadium (III) chloride-(tris-tetrahydrofuran); tungsten hexacarbonyl; palladium 10% on activated carbon; iodine; ammonium formate; zinc; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.04.015

upstream raw materials:

carbon monoxide

(2R,3S,4S,5R)-2,5-diamino-1,6-diphenyl-3,4-hexanediol

N-(benzyloxycarbonyl)-D-phenylalaninol

N-(benzyloxycarbonyl)-D-phenylalaninal

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