ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate

Base Information

• Chemical Name: ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate
• CAS No.: 1380347-51-2
• Molecular Formula: C₂₉H₃₆N₂O₆
• Molecular Weight: 508.615

Synonyms:ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate

Chemical Property of ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate

There total 8 articles about ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate 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:

C29H34N2O6 → ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate (1380347-51-2)

Guidance literature:

C₂₉H₃₄N₂O₆; With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 20 ℃; for 1.08333h; Inert atmosphere;

With methanol; In tetrahydrofuran; toluene; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.04.008

Reference yield:

2-(3-iodophenyl)-5-methyl-1,3-benzoxazole (1380347-27-2) → ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate (1380347-51-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / 1,3-dimethyl-2-imidazolidinone; mineral oil / 0.33 h / 0 - 20 °C / Inert atmosphere

1.2: 4 h / 120 °C / Inert atmosphere

2.1: sodium hydroxide / 1,2-dimethoxyethane; water / 4 h / 60 °C

2.2: 1 h / 90 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / acetonitrile / 1 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / hexane; toluene / 1 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

6.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere

6.2: 0.08 h / 20 °C / Inert atmosphere

With n-butyllithium; borane-THF; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,3-dimethyl-2-imidazolidinone; 1,2-dimethoxyethane; hexane; water; toluene; acetonitrile; mineral oil; 5.1: Horner-Wadsworth-Emmons olefination / 5.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.bmc.2012.04.008

Reference yield:

dimethyl (3-[3-(5-methyl-1,3-benzoxazol-2-yl)phenyl]-2-oxopropyl)phosphonate (1380347-16-9) → ethyl (4R,5E,7S)-8-(3-(5-methyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate (1380347-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

2.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere

2.2: 0.08 h / 20 °C / Inert atmosphere

With borane-THF; sodium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; mineral oil; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.bmc.2012.04.008

upstream raw materials:

(R)-ethyl 4-(tert-butoxycarbonylamino)-5-oxopentanoate

2-(3-iodophenyl)-5-methyl-1,3-benzoxazole

C₂₁H₂₁NO₅

C₁₆H₁₃NO₃

Downstream raw materials:

ethyl 2-((2-[(2R)-2-((1E,3S)-4-[3-(5-methyl-1,3-benzoxazol-2-yl)phenyl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl)thio)-1,3-thiazole-4-carboxylate

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