(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

Base Information

Chemical Name:(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester
CAS No.:1027976-85-7
Molecular Formula:C₂₇H₄₂BrNO₆
Molecular Weight:556.538
Hs Code.:

Synonyms:(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

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Chemical Property of (2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

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Technology Process of (2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

There total 6 articles about (2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic 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:

: 200866-62-2
(R)-2-hexyl-3-(tert-butoxycarbonyl)propionic acid

: 1027976-85-7
(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / -78 - 20 °C

2.1: DBU / benzene / 4 h / Heating

3.1: 9-BBN / tetrahydrofuran / 12 h / 0 - 20 °C

3.2: aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

4.1: CBr₄; PPh₃; imidazole / CH₂Cl₂ / 3.33 h / 0 - 20 °C

5.1: H₂ / Pd/C / methanol / 3 h

6.1: NMM; TBTU / dimethylformamide / 2 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm010127e

Reference yield:

: 2-allyl-3-hexyl-succinic acid 1-tert-butyl ester

: 1027976-85-7
(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: DBU / benzene / 4 h / Heating

2.1: 9-BBN / tetrahydrofuran / 12 h / 0 - 20 °C

2.2: aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

3.1: CBr₄; PPh₃; imidazole / CH₂Cl₂ / 3.33 h / 0 - 20 °C

4.1: H₂ / Pd/C / methanol / 3 h

5.1: NMM; TBTU / dimethylformamide / 2 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm010127e

Reference yield:

: (2R,3S)-2-Allyl-3-hexyl-succinic acid 4-benzyl ester 1-tert-butyl ester

: 1027976-85-7
(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 9-BBN / tetrahydrofuran / 12 h / 0 - 20 °C

1.2: aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

2.1: CBr₄; PPh₃; imidazole / CH₂Cl₂ / 3.33 h / 0 - 20 °C

3.1: H₂ / Pd/C / methanol / 3 h

4.1: NMM; TBTU / dimethylformamide / 2 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm010127e