(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

Base Information

Chemical Name:(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester
CAS No.:1027574-90-8
Molecular Formula:C₂₆H₄₀BrNO₆
Molecular Weight:542.511
Hs Code.:

Synonyms:(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

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Chemical Property of (2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

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Technology Process of (2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

There total 5 articles about (2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic 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:

: 191406-76-5
Benzyl 3S-(3-bromopropyl)-3-t-butoxycarbonyl-2(R)-isobutylpropanoate

: 1027574-90-8
(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / H₂ / Pd/C / methanol / 3 h

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

With 4-methyl-morpholine; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm010127e

Reference yield:

: 191406-75-4
4-benzyl 1-tert-butyl (2S,3R)-2-(3-hydroxypropyl)-3-isobutylbutanedioate

: 1027574-90-8
(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 65 percent / CBr₄; PPh₃; imidazole / CH₂Cl₂ / 3.33 h / 0 - 20 °C

2: 99 percent / H₂ / Pd/C / methanol / 3 h

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

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

Reference yield:

: 191406-74-3
(2R,3S)-3-(tert-butoxycarbonyl)-2-isobutylhex-5-enoic acid benzyl ester

: 1027574-90-8
(2S,3R)-2-(3-Bromo-propyl)-3-[(S)-3-(4-hydroxy-phenyl)-1-methoxycarbonyl-propylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 64 percent / aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

2.1: 65 percent / CBr₄; PPh₃; imidazole / CH₂Cl₂ / 3.33 h / 0 - 20 °C

3.1: 99 percent / 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