(2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide

Base Information

• Chemical Name: (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide
• CAS No.: 119163-36-9
• Molecular Formula: C₁₅H₂₁NO₂
• Molecular Weight: 247.337
• Mol file: 119163-36-9.mol

Synonyms:(2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide

Chemical Property of (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide

There total 3 articles about (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide 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%

(E)-N,N-diisopropylcinnamamide (23795-34-8,119163-14-3) → (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide (119163-36-9)

Guidance literature:

With tert.-butylhydroperoxide; n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 72h;

DOI:10.1039/P19880002663

Reference yield:

N,N-diisopropylchloroacetamide (7403-66-9) + benzaldehyde (100-52-7) → (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide (119163-36-9) + (2S,3S)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide

Guidance literature:

N,N-diisopropylchloroacetamide; With lithium diisopropyl amide; at -78 ℃;

benzaldehyde; With sodium hydride;

DOI:10.1021/jo049021s

Reference yield:

diisopropylamine (108-18-9) → (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid diisopropylamide (119163-36-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / -78 °C

1.2: NaH

With lithium diisopropyl amide;

DOI:10.1021/jo049021s

upstream raw materials:

(E)-N,N-diisopropylcinnamamide

N,N-diisopropylchloroacetamide

benzaldehyde

diisopropylamine

Refernces

• 1、 North, Michael,Pizzato, Francesca. "Diastereoselective darzens condensations of α-haloamides: Influence of aryl substituents on diastereoselectivity". experimental part. p. 552 - 556. Retrieved 2010/04/23.