Oxaziridine, 2-[(1S,2S)-1-[[(4-bromophenyl)methoxy]methyl]-2-methyl-3-butenyl]-3-(4 -methoxyphenyl)-

Base Information

• Chemical Name: Oxaziridine, 2-[(1S,2S)-1-[[(4-bromophenyl)methoxy]methyl]-2-methyl-3-butenyl]-3-(4 -methoxyphenyl)-
• CAS No.: 434308-66-4
• Molecular Formula: C21H24BrNO3
• Molecular Weight: 418.33
• Mol file: 434308-66-4.mol

Synonyms:

Chemical Property of Oxaziridine, 2-[(1S,2S)-1-[[(4-bromophenyl)methoxy]methyl]-2-methyl-3-butenyl]-3-(4 -methoxyphenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Oxaziridine, 2-[(1S,2S)-1-[[(4-bromophenyl)methoxy]methyl]-2-methyl-3-butenyl]-3-(4 -methoxyphenyl)-

There total 10 articles about Oxaziridine, 2-[(1S,2S)-1-[[(4-bromophenyl)methoxy]methyl]-2-methyl-3-butenyl]-3-(4 -methoxyphenyl)- 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:

2-(4-bromobenzyloxy)ethanol (400837-92-5) → 2-[(1S,2S)-1-(4-Bromo-benzyloxymethyl)-2-methyl-but-3-enyl]-3-(4-methoxy-phenyl)-oxaziridine (434308-66-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 24 °C

2.1: n-BuLi; t-BuOK; (+)-(Ipc)2BOMe / BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 5 h / -78 °C

2.2: 45 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; hexane; diethyl ether / 1 h / Heating

3.1: pyridine; DMAP / CH₂Cl₂ / 16 h / 24 °C

4.1: NaN₃ / dimethylformamide / 16 h / 85 °C

5.1: 7.0 mg / PPh₃ / tetrahydrofuran; H₂O / 4 h / 55 °C

6.1: Na₂CO₃ / methanol / 17 h / 24 - 60 °C

7.1: m-CPBA / CH₂Cl₂ / 2 h / 24 °C

With pyridine; dmap; n-butyllithium; sodium azide; potassium tert-butylate; sodium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Dess-Martin oxidation;

DOI:10.1021/jo0486387

Reference yield:

(3S,4R)-5-(4-bromobenzyloxy)-4-hydroxy-3-methylpent-1-ene (434308-60-8) → 2-[(1S,2S)-1-(4-Bromo-benzyloxymethyl)-2-methyl-but-3-enyl]-3-(4-methoxy-phenyl)-oxaziridine (434308-66-4)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine; DMAP / CH₂Cl₂ / 16 h / 24 °C

2: NaN₃ / dimethylformamide / 16 h / 85 °C

3: 7.0 mg / PPh₃ / tetrahydrofuran; H₂O / 4 h / 55 °C

4: Na₂CO₃ / methanol / 17 h / 24 - 60 °C

5: m-CPBA / CH₂Cl₂ / 2 h / 24 °C

With pyridine; dmap; sodium azide; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0486387

Reference yield:

2-((4-bromobenzyl)oxy)acetaldehyde (201341-14-2) → 2-[(1S,2S)-1-(4-Bromo-benzyloxymethyl)-2-methyl-but-3-enyl]-3-(4-methoxy-phenyl)-oxaziridine (434308-66-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi; t-BuOK; (+)-(Ipc)2BOMe / BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 5 h / -78 °C

1.2: 45 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; hexane; diethyl ether / 1 h / Heating

2.1: pyridine; DMAP / CH₂Cl₂ / 16 h / 24 °C

3.1: NaN₃ / dimethylformamide / 16 h / 85 °C

4.1: 7.0 mg / PPh₃ / tetrahydrofuran; H₂O / 4 h / 55 °C

5.1: Na₂CO₃ / methanol / 17 h / 24 - 60 °C

6.1: m-CPBA / CH₂Cl₂ / 2 h / 24 °C

With pyridine; dmap; n-butyllithium; sodium azide; potassium tert-butylate; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0486387

upstream raw materials:

[(1S,2S)-1-(4-Bromo-benzyloxymethyl)-2-methyl-but-3-enyl]-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amine

2-(4-bromobenzyloxy)ethanol

1-bromomethyl-4-bromobenzene

2-((4-bromobenzyl)oxy)acetaldehyde

Downstream raw materials:

p-methoxyl benzaldoxime

(3S,4S)-5-(4-bromobenzyloxy)-4-hydroxylamino-3-methylpent-1-ene

cylindrospermopsin

(3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione

Refernces

• 1、 White, James D.,Hansen, Joshua D.. "Asymmetric synthesis of epicylindrospermopsin via intramolecular nitrone cycloaddition. Assignment of absolute configuration". . p. 4950 - 4951. Retrieved 2007/10/03.