(4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 536972-21-1
• Molecular Formula: C₃₈H₄₄N₂O₅
• Molecular Weight: 608.778
• Mol file: 536972-21-1.mol

Synonyms:(4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 12 articles about (4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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: 76.0%

(4S,5S)-4-Benzyl-5-{(S)-2-benzyl-4-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (177845-02-2) → (4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (536972-21-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jm0204587

Reference yield:

3,3a,8,8a-tetrahydro-2H-indeno[2,1-b]furan-2-one (178032-91-2) → (4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (536972-21-1)

Guidance literature:

Multi-step reaction with 6 steps

1: trimethyl aluminum / benzene / 16 h

2: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

3: 92 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / -78 °C

4: CHCl₃

5: 123.5 mg / KHMDS / tetrahydrofuran; toluene / 0.17 h / 20 °C

6: 76 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; trimethylaluminum; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene; benzene;

DOI:10.1021/jm0204587

Reference yield:

2,2a,7,7a-tetrahydro-cyclobuta[a]inden-1-one (31996-70-0) → (4S,5S)-4-Benzyl-5-[(S)-2-benzyl-4-((1R,2R)-2-hydroxy-indan-1-yl)-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (536972-21-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 20 °C

1.2: 37 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.1: 95 percent / toluene / 30 h / Heating

3.1: 90 percent / aq. AcOH; H₂O₂ / 20 h / 5 °C

4.1: trimethyl aluminum / benzene / 16 h

5.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 92 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / -78 °C

7.1: CHCl₃

8.1: 123.5 mg / KHMDS / tetrahydrofuran; toluene / 0.17 h / 20 °C

9.1: 76 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

With 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; dihydrogen peroxide; trimethylaluminum; potassium hexamethylsilazane; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene; benzene; 3.1: Baeyer-Villiger oxidation;

DOI:10.1021/jm0204587

upstream raw materials:

(4S,5S)-4-Benzyl-5-{(S)-2-benzyl-4-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-3-oxo-2,3-dihydro-1H-pyrrol-2-ylmethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

3,3a,8,8a-tetrahydro-2H-indeno[2,1-b]furan-2-one

2,2a,7,7a-tetrahydro-cyclobuta[a]inden-1-one

(4S,5S)-5-((S)-2-Amino-2-methoxycarbonyl-3-phenyl-propyl)-4-benzyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(4S,5S)-4-Benzyl-5-{(S)-2-benzyl-3-oxo-4-[(1R,2R)-2-(2,2,2-trichloro-acetylcarbamoyloxy)-indan-1-yl]-2,3-dihydro-1H-pyrrol-2-ylmethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester