(4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate
• CAS No.: 408535-08-0
• Molecular Formula: C₂₉H₃₂N₂O₆S
• Molecular Weight: 536.649
• Mol file: 408535-08-0.mol

Synonyms:(4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate

Chemical Property of (4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate

There total 7 articles about (4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate 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: 48.0%

p-toluenesulfonyl chloride (98-59-9) + (2S,3R)-1-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-2-amino-6-hydroxy-3-phenylhexan-1-one (408535-06-8) → (4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate (408535-08-0)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1021/jo010124+

Reference yield:

(4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one (128891-66-7) → (4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate (408535-08-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: copper(I) bromide-dimethyl sulfide complex / tetrahydrofuran / 1.5 h / -78 °C

1.2: 98 percent / tetrahydrofuran / 2.5 h / -78 °C

2.1: BH₃ / tetrahydrofuran / 1 h / 0 °C

2.2: 65 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 3 h / 20 °C

3.1: 100 percent / Ag₂O / CH₂Cl₂ / 48 h

4.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.67 h / -78 °C

4.2: 2,4,6-triisopropylbenzenesulfonyl azide / tetrahydrofuran; toluene / 0.03 h / -78 °C

4.3: 73 percent / acetic acid; potassium acetate / tetrahydrofuran; toluene / 1.5 h / 30 - 35 °C

5.1: 25 percent / H₂ / 10percent Pd/C / ethanol / 10 h / 1551.49 Torr

6.1: 48 percent / pyridine / 0 °C

With pyridine; copper(I) bromide dimethylsulfide complex; borane; hydrogen; potassium hexamethylsilazane; silver(l) oxide; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/jo010124+

Reference yield:

(4S)-3-((3S)-3-phenylhex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one (142078-08-8) → (4R,5S)-6-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-5-amino-6-oxo-4-phenylhexyl 4-methylbenzenesulfonate (408535-08-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BH₃ / tetrahydrofuran / 1 h / 0 °C

1.2: 65 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 3 h / 20 °C

2.1: 100 percent / Ag₂O / CH₂Cl₂ / 48 h

3.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.67 h / -78 °C

3.2: 2,4,6-triisopropylbenzenesulfonyl azide / tetrahydrofuran; toluene / 0.03 h / -78 °C

3.3: 73 percent / acetic acid; potassium acetate / tetrahydrofuran; toluene / 1.5 h / 30 - 35 °C

4.1: 25 percent / H₂ / 10percent Pd/C / ethanol / 10 h / 1551.49 Torr

5.1: 48 percent / pyridine / 0 °C

With pyridine; borane; hydrogen; potassium hexamethylsilazane; silver(l) oxide; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/jo010124+

upstream raw materials:

p-toluenesulfonyl chloride

(2S,3R)-1-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-2-amino-6-hydroxy-3-phenylhexan-1-one

(4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one

(4S)-3-((3S)-3-phenylhex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one