(4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline

Base Information

• Chemical Name: (4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline
• CAS No.: 274681-82-2
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.294
• Mol file: 274681-82-2.mol

Synonyms:(4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline

Chemical Property of (4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline

There total 4 articles about (4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline 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: 62.0%

isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate (274681-81-1) → (4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline (274681-82-2)

Guidance literature:

With potassium hydrogencarbonate; In water; acetone; at 70 ℃; for 20h;

DOI:10.1016/S0040-4020(01)00090-4

Reference yield:

(E)-isopropyl cinnamate (60512-85-8) → (4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline (274681-82-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / LiOH; (DHQ)2-PHAL / K₂Os₂O₂(OH)4

2: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

3: 62 percent / KHCO₃ / acetone; H₂O / 20 h / 70 °C

With lithium hydroxide; (DHQ)2-PHAL; potassium hydrogencarbonate; triethylamine; potassium osmate; In dichloromethane; water; acetone; 1: Sharpless asymmetric aminohydroxylation / 2: Mesylation / 3: Cyclization;

DOI:10.1021/ol005681h

Reference yield:

(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester (195624-97-6) → (4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline (274681-82-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 62 percent / KHCO₃ / acetone; H₂O / 20 h / 70 °C

With potassium hydrogencarbonate; triethylamine; In dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)00090-4

upstream raw materials:

isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate

isopropyl cinnamate

(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester

(E)-isopropyl cinnamate