(R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one

Base Information

• Chemical Name: (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one
• CAS No.: 1267597-50-1
• Molecular Formula: C₂₄H₂₇NO₃
• Molecular Weight: 377.483
• Mol file: 1267597-50-1.mol

Synonyms:(R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one

Chemical Property of (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one

There total 3 articles about (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-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: 94.0%

allyl iodid (556-56-9) + (4R)-N-Propionyl-5,5-diphenyl-4-isopropyloxazolidin-2-one (223906-53-4) → (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one (1267597-50-1)

Guidance literature:

(4R)-N-Propionyl-5,5-diphenyl-4-isopropyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

allyl iodid; In tetrahydrofuran; at -78 ℃; for 18h;

DOI:10.1016/j.tet.2021.132118

Reference yield:

allyl bromide (106-95-6) + (4R)-N-Propionyl-5,5-diphenyl-4-isopropyloxazolidin-2-one (223906-53-4) → (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one (1267597-50-1)

Guidance literature:

(4R)-N-Propionyl-5,5-diphenyl-4-isopropyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -80 ℃; Inert atmosphere;

allyl bromide; In tetrahydrofuran; Inert atmosphere;

DOI:10.1002/chem.201001752

Reference yield:

(R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one (191090-32-1) → (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one (1267597-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexanes / 0 °C / Inert atmosphere

1.2: 12 h / 0 - 24 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 19 h / -78 - 24 °C / Inert atmosphere

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexanes;

DOI:10.1021/ol3000712

upstream raw materials:

allyl bromide

(4R)-N-Propionyl-5,5-diphenyl-4-isopropyloxazolidin-2-one

(R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one

allyl iodid

Downstream raw materials:

(S)-5-(benzyloxy)-4-methylpentan-1-ol

(2S,5S,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-2-methyldec-6-yn-5-ol

[(2S,6S,9S)-10-(benzyloxy)-6-(methoxymethoxy)-9-methyldec-4-yn-2-yloxy](tert-butyl)dimethylsilane

5-[(2S,5R,9S)-9-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)-2-methyldecylthio]-1-phenyl-1H-tetrazole