(4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone

Base Information

• Chemical Name: (4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone
• CAS No.: 756900-16-0
• Molecular Formula: C₂₅H₃₆N₂O₄
• Molecular Weight: 428.572
• Mol file: 756900-16-0.mol

Synonyms:(4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone

Chemical Property of (4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone

There total 13 articles about (4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone 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:

(2R,3R,4S)-1-(benzyloxy)-2,4-dimethyl-3-hydroxy-5-hexene (108814-35-3) → (4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone (756900-16-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

1.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

2.1: 78 percent / imidazole / dimethylformamide / 0 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

3.2: 87 percent / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

4.1: 68 percent / n-Bu₃SnH; AIBN / 0.33 h / 100 °C

5.1: 87 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 11 h / 20 °C

7.1: 88 percent / NaN₃ / dimethylformamide / 20 - 50 °C

8.1: H₂ / Pd/C; Pb/CaCO₃ / ethanol / 1 h / 760.05 Torr

9.1: 97 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 4.25 h / 0 - 20 °C

10.1: NaH / tetrahydrofuran / 0.33 h / -78 °C

10.2: 94 percent / tetrahydrofuran / 20 h / 20 °C

11.1: 100 percent / H₂ / Pd/C / ethanol / 1 h / 20 °C / 760.05 Torr

12.1: DMSO; Et₃N; sulfur trioxide*pyridine / CH₂Cl₂ / 0 - 20 °C

13.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

13.2: 188 mg / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; dmap; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; palladium on activated charcoal; Piperonyl butoxide; calcium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 13.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2004.06.014

Reference yield:

(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-3,6-hexanediol (134961-82-3) → (4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone (756900-16-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 78 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

2.2: 87 percent / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

3.1: 68 percent / n-Bu₃SnH; AIBN / 0.33 h / 100 °C

4.1: 87 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

5.1: Et₃N; DMAP / CH₂Cl₂ / 11 h / 20 °C

6.1: 88 percent / NaN₃ / dimethylformamide / 20 - 50 °C

7.1: H₂ / Pd/C; Pb/CaCO₃ / ethanol / 1 h / 760.05 Torr

8.1: 97 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 4.25 h / 0 - 20 °C

9.1: NaH / tetrahydrofuran / 0.33 h / -78 °C

9.2: 94 percent / tetrahydrofuran / 20 h / 20 °C

10.1: 100 percent / H₂ / Pd/C / ethanol / 1 h / 20 °C / 760.05 Torr

11.1: DMSO; Et₃N; sulfur trioxide*pyridine / CH₂Cl₂ / 0 - 20 °C

12.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

12.2: 188 mg / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; dmap; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; Piperonyl butoxide; calcium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 12.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2004.06.014

Reference yield:

(2S,4R)-1-benzyloxy-6-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexane (756899-97-5) → (4S)-phenyl-3-[(4R,6R)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone (756900-16-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 87 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 11 h / 20 °C

3.1: 88 percent / NaN₃ / dimethylformamide / 20 - 50 °C

4.1: H₂ / Pd/C; Pb/CaCO₃ / ethanol / 1 h / 760.05 Torr

5.1: 97 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 4.25 h / 0 - 20 °C

6.1: NaH / tetrahydrofuran / 0.33 h / -78 °C

6.2: 94 percent / tetrahydrofuran / 20 h / 20 °C

7.1: 100 percent / H₂ / Pd/C / ethanol / 1 h / 20 °C / 760.05 Torr

8.1: DMSO; Et₃N; sulfur trioxide*pyridine / CH₂Cl₂ / 0 - 20 °C

9.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

9.2: 188 mg / tetrahydrofuran / 2 h / 0 °C

With dmap; sodium azide; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; Piperonyl butoxide; calcium carbonate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 9.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2004.06.014

upstream raw materials:

(4S)-3-[(diethylphosphoro)-acetyl]-4-phenyl-2-oxazolidinone

(S)-2-Methylbutyric acid

(2R,3R,4S)-1-(benzyloxy)-2,4-dimethyl-3-hydroxy-5-hexene

(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-3,6-hexanediol

Downstream raw materials:

(4S)-4-phenyl-3-[(3S,4S,6R)-3,4,6-trimethyl-8-((2S)-N-methyl-2-methylbutyramido)-octanoyl]-2-oxazolidinone

(3R,7S,8S,10R,2'S)-kalkitoxin