(4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one
• CAS No.: 147753-93-3
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 147753-93-3.mol

Synonyms:(4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property of (4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

There total 1 articles about (4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-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:

(4S,5R)-3-((R)-2,4-dimethylpent-4-enoyl)-4-methyl-5-phenyloxazolidin-2-one → (4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one (147753-93-3) + (4S,5R)-3-((2R,4R)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:

With thexylborane; dihydrogen peroxide; sodium hydrogencarbonate; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, 36 h, -15 deg C, 2) MeOH, water, 1 h, 0 deg C;

DOI:10.1021/jo00062a048

Reference yield: 98.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one (147753-93-3) → (4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone (147753-89-7)

Guidance literature:

With 1H-imidazole; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00062a048

Reference yield:

(4S,5R)-3-((2R,4S)-5-Hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one (147753-93-3) → (3S,5R,6S)-3,5-dimethyl-6-isopropyl-3,4,5,6-tetrahydropyran-2-one (206123-70-8,648434-47-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / imidazole / CH₂Cl₂ / Ambient temperature

2: 92 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

3: Et₃N, pyridine*SO₃ / dimethylsulfoxide / 30 h / 25 °C

4: tetrahydrofuran / 1 h / Ambient temperature

5: Bu₄NF / tetrahydrofuran / 0.67 h / Heating

6: 100 percent / N-methylmorpholine N-oxide / RuCl₂(Ph₃P)3 / acetone / 5 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; 4-methylmorpholine N-oxide; triethylamine; tris(triphenylphosphine)ruthenium(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; acetone;

DOI:10.1021/jo00062a048

Downstream raw materials:

(4S,5R)-3-<(2'R,4'S)-1'-Oxo-2',4'-dimethyl-5'-<(tert-butyldimethylsilyl)oxy>pentyl>-4-methyl-5-phenyl-2-oxazolidinone

(3S,5R,6S)-3,5-dimethyl-6-isopropyl-3,4,5,6-tetrahydropyran-2-one