(-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

Base Information

Chemical Name:(-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide
CAS No.:1261560-04-6
Molecular Formula:C₂₇H₂₁BrN₂O₃
Molecular Weight:501.379
Hs Code.:

Synonyms:(-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

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Chemical Property of (-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

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Technology Process of (-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

There total 4 articles about (-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide 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%

: 1261559-61-8
(E)-2-[3-(4-bromophenyl)prop-2-enoyl]pyridine-1-oxide

: 1137-96-8,26505-49-7,201024-81-9
N-(benzylidene)aniline N-oxide

: 2-[(3S,4S,5S)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

: 2-[(3R,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

: 1261560-04-6
(-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

Guidance literature:: (E)-2-[3-(4-bromophenyl)prop-2-enoyl]pyridine-1-oxide; With (4'S,5'S)-2,2-bis[4'-(triisopropylsilyl)-oxymethy-5'-phenyl-1',3'-oxazolin-2'-yl]propane; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; for 0.166667h;

N-(benzylidene)aniline N-oxide; In dichloromethane; at -20 ℃; optical yield given as %ee; enantioselective reaction; Molecular sieve;
DOI:10.1002/chem.201002017

Reference yield:

: 883838-79-7
C₁₄H₁₀BrNO₂

: 1137-96-8,26505-49-7,201024-81-9
N-(benzylidene)aniline N-oxide

: 2-[(3S,4S,5S)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

: 2-[(3R,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

: 1261560-04-6
(-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

Guidance literature:: C₁₄H₁₀BrNO₂; With copper(II) bis(trifluoromethanesulfonate); 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; In ethyl acetate; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

N-(benzylidene)aniline N-oxide; In ethyl acetate; for 10h; optical yield given as %ee; enantioselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/ol102716e

Reference yield:

: 100-52-7
benzaldehyde

: 2-[(3S,4S,5S)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

: 2-[(3R,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

: 1261560-04-6
(-)-2-[(3S,4R,5R)-5-(4-bromophenyl)-2,3-diphenyl-isoxazolidine-4-carbonyl]pyridine-1-oxide

Guidance literature:: Multi-step reaction with 2 steps

1.1: ethanol / 20 °C / Darkness

2.1: copper(II) bis(trifluoromethanesulfonate); 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] / ethyl acetate / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 10 h / Molecular sieve; Inert atmosphere

With copper(II) bis(trifluoromethanesulfonate); 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; In ethanol; ethyl acetate; 2.1: 1,3-dipolar cycloaddition / 2.2: 1,3-dipolar cycloaddition;
DOI:10.1021/ol102716e