(4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone

Base Information

• Chemical Name: (4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone
• CAS No.: 105943-89-3
• Molecular Formula: C₂₇H₂₇NO₄
• Molecular Weight: 429.516
• Mol file: 105943-89-3.mol

Synonyms:(4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone

Chemical Property of (4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone

There total 4 articles about (4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone 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: 88.0%

Benzyloxymethyl chloride (3587-60-8) + (4R,5S)-3-(3-phenylpropionyl)-4-methyl-5-phenyl-oxazolidin-2-one (95841-14-8) → (4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone (105943-89-3)

Guidance literature:

(4R,5S)-3-(3-phenylpropionyl)-4-methyl-5-phenyl-oxazolidin-2-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1.08333h; Inert atmosphere;

Benzyloxymethyl chloride; In dichloromethane; at 0 ℃; for 5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/cbic.201300325

Reference yield:

benzyl bromomethyl ether (17690-16-3) + (4R,5S)-3-(3-phenylpropionyl)-4-methyl-5-phenyl-oxazolidin-2-one (95841-14-8) → (4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone (105943-89-3)

Guidance literature:

With lithium hexamethyldisilazane; Yield given. Multistep reaction; 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 deg C to 0 deg C, 5.5 h;

Reference yield:

(4R,5S)-(+)-4-methyl-5-phenyloxazolidin (591733-72-1) → (4S,5S)-3-<(2S)-2-benzyl-3-(benzyloxy)propionyl>-4-methyl-5-phenyloxazolidinone (105943-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 4.25 h / -78 - 20 °C / Inert atmosphere

2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.08 h / 0 °C / Inert atmosphere

2.2: 5 h / 0 °C / Inert atmosphere

With n-butyllithium; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/cbic.201300325

upstream raw materials:

benzyl bromomethyl ether

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

Benzyloxymethyl chloride

(4R,5S)-(+)-4-methyl-5-phenyloxazolidin

Downstream raw materials:

(2R,4S,5S)-2-Benzyl-4-hydroxy-7-methyl-5-[(S)-3-methyl-2-(3-methyl-butyrylamino)-butyrylamino]-octanoic acid [(S)-1-(3-methyl-butylcarbamoyl)-ethyl]-amide

N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid