(3R,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester

Base Information

• Chemical Name: (3R,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester
• CAS No.: 906109-10-2
• Molecular Formula: C₂₂H₃₂N₂O₆
• Molecular Weight: 420.506
• Mol file: 906109-10-2.mol

Synonyms:

Chemical Property of (3R,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester

There total 1 articles about (3R,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester 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: 56.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + (Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]benzylamine N-oxide (158723-45-6,188965-45-9) → (3S,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester + (3S,5S)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester + (3R,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester (906109-10-2) + (3R,5S)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester

Guidance literature:

at 90 ℃; for 5h;

DOI:10.1016/j.tetlet.2006.05.114

Reference yield:

(3R,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester (906109-10-2) → 5-[1-tert-butoxycarbonylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / H₂ / Pd(OH)2-C / 20 °C / 76000 Torr

2: imidazole / dimethylformamide / 70 °C

3: Et₃N; DMAP / CH₂Cl₂

4: p-TsOH / methanol / 6 h / 45 °C

With 1H-imidazole; dmap; hydrogen; toluene-4-sulfonic acid; triethylamine; palladium hydroxide - carbon; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.05.114

Reference yield:

(3R,5R)-2-Benzyl-3-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-isoxazolidine-5-carboxylic acid methyl ester (906109-10-2) → 4-[1-tert-butoxycarbonyl-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-pyrrolidin-2-yl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (906109-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / H₂ / Pd(OH)2-C / 20 °C / 76000 Torr

2: imidazole / dimethylformamide / 70 °C

3: Et₃N; DMAP / CH₂Cl₂

With 1H-imidazole; dmap; hydrogen; triethylamine; palladium hydroxide - carbon; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.05.114

upstream raw materials:

acrylic acid methyl ester

(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]benzylamine N-oxide

Downstream raw materials:

3-benzoyloxy-5-(1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

4-(4-benzoyloxy-1-tert-butoxycarbonyl-5-oxo-pyrrolidin-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

4-[1-tert-butoxycarbonyl-4-(tert-butyl-diphenyl-silanyloxy)-5-oxo-pyrrolidin-2-yl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester