ethyl (2R,3S)-3-(4-nitrophenyl)oxirane-2-carboxylate

Base Information

• Chemical Name: ethyl (2R,3S)-3-(4-nitrophenyl)oxirane-2-carboxylate
• CAS No.: 54679-39-9
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.212
• DSSTox Substance ID: DTXSID90457302
• Nikkaji Number: J1.907.748I
• Wikidata: Q82280105
• Mol file: 54679-39-9.mol

Synonyms:CTK1E3037;DTXSID90457302;54679-39-9;(2R)-3alpha-(4-Nitrophenyl)oxirane-2beta-carboxylic acid ethyl ester

Chemical Property of ethyl (2R,3S)-3-(4-nitrophenyl)oxirane-2-carboxylate

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 237.06372245
• Heavy Atom Count: 17
• Complexity: 306

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C(O1)C2=CC=C(C=C2)[N+](=O)[O-]
• Isomeric SMILES: CCOC(=O)[C@H]1[C@@H](O1)C2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of ethyl (2R,3S)-3-(4-nitrophenyl)oxirane-2-carboxylate

There total 2 articles about ethyl (2R,3S)-3-(4-nitrophenyl)oxirane-2-carboxylate 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: 68.0%

(methyl-phenyl-amino)-acetic acid ethyl ester (21911-74-0) + 4-nitrobenzaldehdye (555-16-8) → ethyl trans-3-(4-nitrophenyl)oxirane-2-carboxylate (54679-39-9,54679-40-2,109844-94-2)

Guidance literature:

With 2-(trimethylsilyl)phenyl trifluoromethanesulfonate; cesium fluoride; In acetonitrile; at 60 ℃; for 24h; Sealed tube;

DOI:10.1016/j.tet.2018.11.065

Reference yield:

→ ethyl (2RS,3RS)-3-(4-nitrophenyl)-2-oxirane carboxylate (54679-39-9,54679-40-2,109844-94-2)

Guidance literature:

Reference yield:

ethyl (2RS,3RS)-3-(4-nitrophenyl)-2-oxirane carboxylate (54679-39-9,54679-40-2,109844-94-2) → ethyl (2RS,3RS)-3-azido-2-hydroxy-3-(4-nitrophenyl)propanoate

Guidance literature:

With sodium azide; In ethanol; water; formic acid ethyl ester; at 50 ℃;

upstream raw materials:

(methyl-phenyl-amino)-acetic acid ethyl ester

4-nitrobenzaldehdye