(4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one
• CAS No.: 157220-39-8
• Molecular Formula: C₂₃H₂₇NO₅
• Molecular Weight: 397.471
• Mol file: 157220-39-8.mol

Synonyms:(4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property of (4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

There total 1 articles about (4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one 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: 85.0%

3-Benzyloxypropanal (19790-60-4) + (4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) → (4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one (157220-39-8)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; 1.) 0 deg C; 2.) -78 to 0 deg C;

DOI:10.1016/0040-4039(94)88035-2

Reference yield:

(4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one (157220-39-8) → (2S,3R,6S,7S,8R,9S)-2-((2R,3R)-5-Methoxy-3-methyl-tetrahydro-furan-2-yl)-6,8-dimethyl-11-phenylsulfanyl-7,9-bis-triethylsilanyloxy-undecan-3-ol

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) trimethylaluminum / 1.) THF, toluene, 0 deg C -> room temperature, 2.) THF, toluene, CH₂Cl₂, -10 -> 0 deg C

2: 100 percent / imidazole / dimethylformamide / 0.58 h / 23 °C

3: 98 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C

4: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

5: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 °C

6: 99 percent / molecular sieves 4A, titanium tetraisopropoxide, (-)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 2 h / -23 °C

7: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 0 deg C

8: 99 percent / trubutylphosphine / dimethylformamide / 4 h / 23 °C

9: 100 percent / imidazole / dimethylformamide / 2.5 h / 23 °C

10: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 23 °C

11: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 3 h

12: 673 mg / NaH₂PO₄, sodium amalgam / methanol / 2 h / 0 °C

13: 98 percent / calcium, liquid ammonia / tetrahydrofuran; propan-2-ol / 1 h / -78 °C

14: 91 percent / hydrogen / Rh on alumina / ethanol / 1.6 h / 23 °C

15: 99 percent / trubutylphosphine / dimethylformamide / 14 h / 23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium dihydrogenphosphate; sodium amalgam; copper(l) iodide; n-butyllithium; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; ammonia; hydrogen; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; calcium; (-)-diethyl tartrate; 3-chloro-benzenecarboperoxoic acid; rhodium on alumina; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1021/jo9606113

Reference yield:

(4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one (157220-39-8) → (2S,3R,6S,7S,8R,9S)-11-Benzenesulfonyl-2-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-6,8-dimethyl-7,9-bis-triethylsilanyloxy-undecan-3-ol

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) trimethylaluminum / 1.) THF, toluene, 0 deg C -> room temperature, 2.) THF, toluene, CH₂Cl₂, -10 -> 0 deg C

2: 100 percent / imidazole / dimethylformamide / 0.58 h / 23 °C

3: 98 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C

4: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

5: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 °C

6: 99 percent / molecular sieves 4A, titanium tetraisopropoxide, (-)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 2 h / -23 °C

7: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 0 deg C

8: 99 percent / trubutylphosphine / dimethylformamide / 4 h / 23 °C

9: 100 percent / imidazole / dimethylformamide / 2.5 h / 23 °C

10: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 23 °C

11: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 3 h

12: 673 mg / NaH₂PO₄, sodium amalgam / methanol / 2 h / 0 °C

13: 98 percent / calcium, liquid ammonia / tetrahydrofuran; propan-2-ol / 1 h / -78 °C

14: 91 percent / hydrogen / Rh on alumina / ethanol / 1.6 h / 23 °C

15: 99 percent / trubutylphosphine / dimethylformamide / 14 h / 23 °C

16: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium dihydrogenphosphate; sodium amalgam; copper(l) iodide; n-butyllithium; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; ammonia; hydrogen; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; calcium; (-)-diethyl tartrate; 3-chloro-benzenecarboperoxoic acid; rhodium on alumina; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1021/jo9606113

upstream raw materials:

3-Benzyloxypropanal

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

Downstream raw materials:

(2R,3S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide

(E)-(4S,5S)-7-Benzyloxy-4-methyl-5-triethylsilanyloxy-hept-2-en-1-ol

(2S,3S,4S,5S)-7-Benzyloxy-2,4-dimethyl-5-triethylsilanyloxy-heptane-1,3-diol

(2R,3S)-5-Benzyloxy-2-methyl-3-triethylsilanyloxy-pentanoic acid methoxy-methyl-amide