(4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Base Information

• Chemical Name: (4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-2-oxazolidinone
• CAS No.: 77877-24-8
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• Mol file: 77877-24-8.mol

Synonyms:(4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property of (4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

There total 2 articles about (4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-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: 91.0%

pentanal (110-62-3) + (4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) → (4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-2-oxazolidinone (77877-24-8)

Guidance literature:

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.5h;

pentanal; In dichloromethane; a) -78 deg C, 30 min, b) RT, 1.5 h;

DOI:10.1016/S0957-4166(99)00528-5

Reference yield:

4-methyl-5-phenyloxazolidin-2-one (77943-39-6) → (4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-2-oxazolidinone (77877-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: n-BuLi / tetrahydrofuran / -78 °C

2: 1.) boron triflate, diisopropylethylamine, 3.) 30percent hydrogen peroxide

With n-butyllithium; tris(trifluoromethanesulfonyloxy)boron; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja00398a058

Reference yield:

(4R,5S)-[(2R,3S)-3-hydroxy-2-methylheptanoyl]-4-methyl-5-phenyl-2-oxazolidinone (77877-24-8) → (2S,3S)-2-methyl-1-tosyloxy-3-heptanol (260395-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / LiBH₄ / diethyl ether / 2 h / 0 - 20 °C

2: 83 percent / pyridine / CH₂Cl₂ / 14 h / 20 °C

With pyridine; lithium borohydride; In diethyl ether; dichloromethane; 1: Reduction / 2: Tosylation;

DOI:10.1016/S0957-4166(99)00528-5

upstream raw materials:

pentanal

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

4-methyl-5-phenyloxazolidin-2-one

Downstream raw materials:

(4S,5S)-4-Methyl-5-nonanol

(2S,3S)-2-methyl-1-tosyloxy-3-heptanol