((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester

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Chemical Name:((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester
CAS No.:191408-27-2
Molecular Formula:C₃₅H₄₈BrN₃O₆
Molecular Weight:686.687
Hs Code.:

Synonyms:((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester

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Chemical Property of ((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester

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Technology Process of ((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester

There total 8 articles about ((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic 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: 74.0%

: 821-06-7
(E)-1,4-dibromobutene

: 191408-26-1
{(S)-4-[(E)-(R)-2-((S)-2-Benzyloxy-1-hydroxy-ethyl)-5-phenyl-pent-4-enoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester

: 191408-27-2
((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1016/S0960-894X(99)00215-2

Reference yield:

: 14618-80-5
(R)-benzyl glycidol

: 191408-27-2
((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-BuLi, HMPA, 2.) NBS, aq. NaHCO₃ / 1.) THF

2: 1.) LDA, 2.) TMEDA / 1.) THF, from -45 to -20 deg C, 1.5 h, 2.) THF, from -45 to -20 deg C, 3 h

3: aq. NaOH / methanol

4: BOP, i-Pr₂NEt / dimethylformamide

5: 74 percent / NaH / dimethylformamide / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(99)00215-2

Reference yield:

: 147849-60-3
Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate

: 191408-27-2
((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LDA, 2.) TMEDA / 1.) THF, from -45 to -20 deg C, 1.5 h, 2.) THF, from -45 to -20 deg C, 3 h

2: aq. NaOH / methanol

3: BOP, i-Pr₂NEt / dimethylformamide

4: 74 percent / NaH / dimethylformamide / 0 °C

With sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(99)00215-2