(4R,6S,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine

Base Information

• Chemical Name: (4R,6S,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine
• CAS No.: 1335214-60-2
• Molecular Formula: C₂₉H₃₆BrNO₄
• Molecular Weight: 542.513
• Mol file: 1335214-60-2.mol

Synonyms:

Chemical Property of (4R,6S,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6S,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine

There total 4 articles about (4R,6S,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine 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:

(4R,6R,7R,8S)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-3-methyl-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine 2-oxide (1335214-43-1) → (4R,6R,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine (1335214-46-4) + (4R,6S,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine (1335214-60-2)

Guidance literature:

With trimethylsilyl bromide; triethylamine; In acetonitrile; at -30 ℃; for 48h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo201331h

Reference yield:

isovanillin (621-59-0) → (4R,6R,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine (1335214-46-4) + (4R,6S,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine (1335214-60-2)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / Reflux

2: ammonium acetate / Heating

3: tin(IV) chloride / dichloromethane / -94 °C

4: trimethylsilyl bromide; triethylamine / acetonitrile / 18 h / -25 °C / Inert atmosphere

With trimethylsilyl bromide; ammonium acetate; tin(IV) chloride; potassium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c3ob41646a

Reference yield:

(1R,2S)-trans-2-phenylcyclohexanol (98919-68-7) → (4R,6R,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine (1335214-46-4) + (4R,6S,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine (1335214-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: mercury(II) diacetate / 24 h / 25 °C

2: tin(IV) chloride / dichloromethane / 0.17 h / -90 °C / Inert atmosphere

3: trimethylsilyl bromide; triethylamine / acetonitrile / 48 h / -30 °C / Inert atmosphere

With trimethylsilyl bromide; mercury(II) diacetate; tin(IV) chloride; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo201331h

upstream raw materials:

(4R,6R,7R,8S)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-3-methyl-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine 2-oxide

(1R,2S)-trans-2-phenylcyclohexanol

(1R,2S)-2-phenylcyclohexyl vinyl ether

isovanillin