2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid

Base Information

• Chemical Name: 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid
• CAS No.: 72155-54-5
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.24
• Mol file: 72155-54-5.mol

Synonyms:2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid

Chemical Property of 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid

There total 16 articles about 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid 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: 71.0%

(4S,5S)-4-benzyl-5-(2-hydroxyethyl)-2-oxazolidinone (124754-71-8) → 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid (72155-54-5)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 0.5h;

DOI:10.1246/cl.1992.2265

Reference yield:

phosgene (75-44-5) + (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid (72155-50-1,153061-61-1) → 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid (72155-54-5)

Guidance literature:

With potassium hydroxide; In toluene; at 5 ℃; for 1h;

DOI:10.1021/jm00175a006

Reference yield:

(2R,3S)-3-hydroxy-2-methoxycarbonylamino-4-pentenal dimethyl acetal (146552-57-0) → 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid (72155-54-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / CH₃ONa / methanol / 0.5 h / Ambient temperature

2: 88 percent / conc. HCl / dioxane / 2 h / Ambient temperature

3: 66 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) 0 deg C, 1 h

4: 95 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) 9-BBN, 2.) aq. NaHCO₃, H₂O₂ / 1.) THF, RT, 3 h, 2.) THF, EtOH, RT, 40 min

6: 84 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 44 h / 760 Torr

7: 71 percent / Jones reagent / acetone / 0.67 h

With pyridine; hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydrogencarbonate; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; acetone;

DOI:10.1246/bcsj.69.1737

upstream raw materials:

phosgene

(3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid

(4S,5S)-4-benzyl-5-(2-hydroxyethyl)-2-oxazolidinone

(4R,5S)-2-oxo-5-vinyl-oxazolidine-4-carbaldehyde dimethyl acetal

Downstream raw materials:

methyl (4S,5S)-4-benzyl-2-oxooxazolidine-5-acetate