Oxirane, triphenyl-, (3R)-

Base Information

• Chemical Name: Oxirane, triphenyl-, (3R)-
• CAS No.: 183849-26-5
• Molecular Formula: C20H16O
• Molecular Weight: 272.346
• DSSTox Substance ID: DTXSID00454766
• Nikkaji Number: J857.981D
• Mol file: 183849-26-5.mol

Synonyms:Oxirane, triphenyl-, (3R)-;183849-26-5;2,2,3beta-Triphenyloxirane;SCHEMBL7108506;DTXSID00454766

Chemical Property of Oxirane, triphenyl-, (3R)-

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 272.120115130
• Heavy Atom Count: 21
• Complexity: 314

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(O2)(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]2C(O2)(C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of Oxirane, triphenyl-, (3R)-

There total 8 articles about Oxirane, triphenyl-, (3R)- 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: 75.0%

(3S)-2,2-diphenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]oxirane (1029690-06-9) → (S)-2,2,3-triphenyloxirane (157556-88-2) + (R)-2,2,3-triphenyloxirane (183849-26-5)

Guidance literature:

(3S)-2,2-diphenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]oxirane; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ol8005387

Reference yield: 74.0%

Triphenylethylene (58-72-0) → (R)-2,2,3-triphenyloxirane (183849-26-5)

Guidance literature:

With Oxone; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; sodium hydrogencarbonate; methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-arabinohexopyranosid-3-ulose; In 1,2-dimethoxyethane; water; at 0 ℃; pH=8; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tet.2011.07.014

Reference yield: 70.0%

(S)-1,1,2-triphenyl-1,2-ethanediol (108998-83-0) → (R)-2,2,3-triphenyloxirane (183849-26-5)

Guidance literature:

With tributylphosphine; di-isopropyl azodicarboxylate; In dichloromethane; at 20 ℃;

DOI:10.1021/ol0629420

upstream raw materials:

Triphenylethylene

(S)-1,1,2-triphenyl-1,2-ethanediol

(S)-(-)-ethyl mandelate

(3S)-2,2-diphenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]oxirane

Downstream raw materials:

α-phenylbenzoin