(4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole

Base Information

• Chemical Name: (4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole
• CAS No.: 114839-34-8
• Molecular Formula: C₂₈H₃₅NO₇
• Molecular Weight: 497.588
• Mol file: 114839-34-8.mol

Synonyms:(4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole

Chemical Property of (4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole

There total 5 articles about (4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole 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: 72.0%

4-lithio-1,2-dimethoxybenzene (80245-51-8) + L-trans-threonine oxazoline (114839-33-7) → (4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole (114839-34-8)

Guidance literature:

In tetrahydrofuran; 1.) - 20 deg C, 15 h; 2.) roomtemp., 4 h;

DOI:10.1021/ja00222a021

Reference yield:

4-Bromoveratrole (2859-78-1) → (4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole (114839-34-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tert-butyllithium / tetrahydrofuran; pentane / -78 °C

2: 72 percent / tetrahydrofuran / 1.) - 20 deg C, 15 h; 2.) roomtemp., 4 h

With tert.-butyl lithium; In tetrahydrofuran; pentane;

DOI:10.1021/ja00222a021

Reference yield:

2,3-Dimethoxy-7-methyl-naphthalin-6-carbonsaeure-ethylester (79150-37-1) → (4R,5R)-2-[(1R,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-3-methoxymethyl-1,2-dihydro-naphthalen-2-yl]-4-methoxymethyl-5-methyl-4,5-dihydro-oxazole (114839-34-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / N-bromosuccinimide / CCl₄; hexane / 24 h / Heating

2: 1.) K₂CO₃; 2.) 2M aq. sodium hydroxide / 1.) methanol, 24 h; 2.) water, reflux

3: 1.) CCl₄, triethylamine, triphenylphosphine; 2.) 1M HCl / 1.) pyridine-acetonitrile, 2 h; 2.) methanol-water, 0 deg C, 10 min

4: 72 percent / tetrahydrofuran / 1.) - 20 deg C, 15 h; 2.) roomtemp., 4 h

With hydrogenchloride; tetrachloromethane; sodium hydroxide; N-Bromosuccinimide; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; hexane;

DOI:10.1021/ja00222a021

upstream raw materials:

4-lithio-1,2-dimethoxybenzene

L-trans-threonine oxazoline

4-Bromoveratrole

2,3-Dimethoxy-7-methyl-naphthalin-6-carbonsaeure-ethylester

Downstream raw materials:

(R)-32

(S)-32

(+)-phyltetralin

(-)-demethylphyltetralin