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

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Chemical Name:(4R)-phenyl-3-[(4R,6S)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone
CAS No.:320742-90-3
Molecular Formula:C₂₅H₃₆N₂O₄
Molecular Weight:428.572
Hs Code.:

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

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

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

There total 12 articles about (4R)-phenyl-3-[(4R,6S)-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:

: 128329-63-5
(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol

: 320742-90-3
(4R)-phenyl-3-[(4R,6S)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone

Guidance literature:: Multi-step reaction with 8 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

2.1: 87 percent / NaN₃ / dimethylformamide / 20 °C

3.1: H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

4.1: 826 mg / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 0 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

5.2: 83 percent / tetrahydrofuran; hexane / -78 - 20 °C

6.1: 94 percent / TBAF / tetrahydrofuran / 0 - 20 °C

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

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

8.2: 333 mg / tetrahydrofuran / 2 h / 0 °C

With dmap; n-butyllithium; sodium azide; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2004.06.014

Reference yield:

: 198124-61-7
(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol

: 320742-90-3
(4R)-phenyl-3-[(4R,6S)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone

Guidance literature:: Multi-step reaction with 11 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: 63 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

3.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

3.2: 71 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

5.1: 87 percent / NaN₃ / dimethylformamide / 20 °C

6.1: H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

7.1: 826 mg / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 0 - 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.2: 83 percent / tetrahydrofuran; hexane / -78 - 20 °C

9.1: 94 percent / TBAF / tetrahydrofuran / 0 - 20 °C

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

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

11.2: 333 mg / tetrahydrofuran / 2 h / 0 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; sodium azide; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 11.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2004.06.014

Reference yield:

: 320742-72-1
(2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene

: 320742-90-3
(4R)-phenyl-3-[(4R,6S)-4,6-dimethyl-8-((2S)-N-methyl-2-methylbutyramido)-(E)-2-octenoyl]-2-oxazolidinone

Guidance literature:: Multi-step reaction with 9 steps

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

1.2: 71 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

3.1: 87 percent / NaN₃ / dimethylformamide / 20 °C

4.1: H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

5.1: 826 mg / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 0 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.2: 83 percent / tetrahydrofuran; hexane / -78 - 20 °C

7.1: 94 percent / TBAF / tetrahydrofuran / 0 - 20 °C

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

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

9.2: 333 mg / tetrahydrofuran / 2 h / 0 °C

With dmap; n-butyllithium; sodium azide; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 9.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2004.06.014