(4R,5S)-3-[(2R,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-[(2R,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one
• CAS No.: 220392-62-1
• Molecular Formula: C₂₂H₃₁NO₄Si
• Molecular Weight: 401.578
• Mol file: 220392-62-1.mol

Synonyms:(4R,5S)-3-[(2R,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property of (4R,5S)-3-[(2R,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-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,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one

There total 1 articles about (4R,5S)-3-[(2R,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-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: 80.0%

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) + 3-(tert-butyldimethylsilyl)-2-propynal (90083-19-5) → (4R,5S)-3-[(2R,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one (220392-62-1)

Guidance literature:

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1.5h;

3-(tert-butyldimethylsilyl)-2-propynal; In dichloromethane; at -78 - 0 ℃; for 2.5h; Further stages.;

DOI:10.1002/1521-3765(20000602)6:11<1987::AID-CHEM1987>3.0.CO;2-U

Reference yield:

(4R,5S)-3-[(2R,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one (220392-62-1) → reveromycin B

Guidance literature:

Multi-step reaction with 14 steps

1.1: 90 percent / AlMe₃ / tetrahydrofuran; toluene / 2 h / -30 - 0 °C

2.1: TBAF/SiO₂ / tetrahydrofuran / 3 h / 25 °C

3.1: 938 mg / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 25 °C

4.1: DIBAL-H / tetrahydrofuran; toluene / 0.5 h / -78 °C

5.1: 1.76 g / CH₂Cl₂ / 15 h / 25 °C

6.1: nBu₃SnH / [Pd(PPh₃)2Cl₂] / benzene / 0.17 h / 5 °C

6.2: 140 mg / I₂ / CH₂Cl₂ / 0.08 h / 0 °C

7.1: CpZrHCl / tetrahydrofuran / 2 h / 50 °C

7.2: ZnCl₂ / tetrahydrofuran / 0.08 h / 25 °C

7.3: 84 percent / [Pd(PPh₃)4] / tetrahydrofuran / 2 h / 25 °C

8.1: 75 percent / PPTS; MeOH / 3 h / 40 °C

9.1: 95 percent / aq. NaIO₄ / tetrahydrofuran / 2 h / 0 - 25 °C

10.1: 35 percent / CrCl₂; NiCl₂ / dimethylformamide / 2 h / 25 °C

11.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 25 °C

12.1: CeCl₃*7H₂O; LiBH₄ / tetrahydrofuran; methanol / 3 h / -78 - 25 °C

13.1: 85 percent / DMAP / CH₂Cl₂ / 3 h / 25 °C

14.1: 69 percent / DBAF / tetrahydrofuran / 2 h / 25 °C

With 2,6-dimethylpyridine; chromium dichloride; methanol; dmap; sodium periodate; lithium borohydride; cerium(III) chloride; CpZrHCl; tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; silica gel; diisobutylaluminium hydride; Dess-Martin periodane; nickel dichloride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: Substitution / 2.1: Desilylation / 3.1: Etherification / 4.1: Reduction / 5.1: Condensation / 6.1: Addition / 6.2: Substitution / 7.1: Addition / 7.2: Transmetallation / 7.3: Negishi coupling / 8.1: Methanolysis / 9.1: Oxidation / 10.1: Addition / 11.1: Oxidation / 12.1: Reduction / 13.1: Esterification / 14.1: Silyl ether cleavage, Ether cleavage;

DOI:10.1002/1521-3765(20000602)6:11<1987::AID-CHEM1987>3.0.CO;2-U

Reference yield:

(4R,5S)-3-[(2R,3R)-5-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-2-methyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one (220392-62-1) → C19-epi-reveromycin B

Guidance literature:

Multi-step reaction with 12 steps

1.1: 90 percent / AlMe₃ / tetrahydrofuran; toluene / 2 h / -30 - 0 °C

2.1: TBAF/SiO₂ / tetrahydrofuran / 3 h / 25 °C

3.1: 938 mg / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 25 °C

4.1: DIBAL-H / tetrahydrofuran; toluene / 0.5 h / -78 °C

5.1: 1.76 g / CH₂Cl₂ / 15 h / 25 °C

6.1: nBu₃SnH / [Pd(PPh₃)2Cl₂] / benzene / 0.17 h / 5 °C

6.2: 140 mg / I₂ / CH₂Cl₂ / 0.08 h / 0 °C

7.1: CpZrHCl / tetrahydrofuran / 2 h / 50 °C

7.2: ZnCl₂ / tetrahydrofuran / 0.08 h / 25 °C

7.3: 84 percent / [Pd(PPh₃)4] / tetrahydrofuran / 2 h / 25 °C

8.1: 75 percent / PPTS; MeOH / 3 h / 40 °C

9.1: 95 percent / aq. NaIO₄ / tetrahydrofuran / 2 h / 0 - 25 °C

10.1: 35 percent / CrCl₂; NiCl₂ / dimethylformamide / 2 h / 25 °C

11.1: 88 percent / DMAP / CH₂Cl₂ / 3 h / 25 °C

12.1: 61 percent / DBAF / tetrahydrofuran / 2 h / 25 °C

With 2,6-dimethylpyridine; chromium dichloride; methanol; dmap; sodium periodate; CpZrHCl; tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; silica gel; diisobutylaluminium hydride; nickel dichloride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: Substitution / 2.1: Desilylation / 3.1: Etherification / 4.1: Reduction / 5.1: Condensation / 6.1: Addition / 6.2: Substitution / 7.1: Addition / 7.2: Transmetallation / 7.3: Negishi coupling / 8.1: Methanolysis / 9.1: Oxidation / 10.1: Addition / 11.1: Esterification / 12.1: Silyl ether cleavage, Ether cleavage;

DOI:10.1002/1521-3765(20000602)6:11<1987::AID-CHEM1987>3.0.CO;2-U

upstream raw materials:

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

3-(tert-butyldimethylsilyl)-2-propynal