tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate

Base Information

• Chemical Name: tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate
• CAS No.: 907189-15-5
• Molecular Formula: C₃₀H₄₅NO₉
• Molecular Weight: 563.689

Synonyms:tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate

Chemical Property of tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate

There total 7 articles about tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate 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: 28.0%

(S)-2-((2S,4S)-4-tert-butyloxycarbonylmethyl-2-tert-butyl-5-oxo-1,3-dioxolan-4-yl)-3-butenoic acid (907189-06-4) + 2-amino-3-(4-tert-butoxy-phenyl)-propionic acid tert-butyl ester (17083-23-7) → 2-{1-[1-tert-butoxycarbonyl-2-(4-tert-butoxy-phenyl)-ethylcarbamoyl]-allyl}-2-hydroxy-succinic acid dimethyl ester + tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate (907189-15-5)

Guidance literature:

(S)-2-((2S,4S)-4-tert-butyloxycarbonylmethyl-2-tert-butyl-5-oxo-1,3-dioxolan-4-yl)-3-butenoic acid; With potassium carbonate; In methanol; at 25 ℃; for 18h;

2-amino-3-(4-tert-butoxy-phenyl)-propionic acid tert-butyl ester; With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 2h;

DOI:10.1021/jo060931e

Reference yield:

(2S,3S)-2-hydroxy-3-(hydroxycarbonyl)-4-pentenoic acid (907189-03-1) → tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate (907189-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: i-Pr₂NEt / tetrahydrofuran / 2 h / 25 °C

2.1: 79 percent / Me₃SiOTf / CH₂Cl₂ / 16 h / -35 °C

3.1: lithium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0.83 h / -70 °C

3.2: 61 percent / tetrahydrofuran; dimethylformamide / 0.25 h / -70 °C

4.1: K₂CO₃ / methanol / 18 h / 25 °C

4.2: 28 percent / 1-hydroxy-1,2,3-benzotriazole; i-Pr₂NEt; HBTU / dimethylformamide / 2 h / 0 - 25 °C

With trimethylsilyl trifluoromethanesulfonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo060931e

Reference yield:

(2S,3S)-2-hydroxy-3-(hydroxycarbonyl)-4-pentenoate (907189-18-8) → tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-5-hexenoate (907189-15-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LiOH / methanol; H₂O / 20 °C

2.1: i-Pr₂NEt / tetrahydrofuran / 2 h / 25 °C

3.1: 79 percent / Me₃SiOTf / CH₂Cl₂ / 16 h / -35 °C

4.1: lithium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0.83 h / -70 °C

4.2: 61 percent / tetrahydrofuran; dimethylformamide / 0.25 h / -70 °C

5.1: K₂CO₃ / methanol / 18 h / 25 °C

5.2: 28 percent / 1-hydroxy-1,2,3-benzotriazole; i-Pr₂NEt; HBTU / dimethylformamide / 2 h / 0 - 25 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo060931e

upstream raw materials:

(S)-2-((2S,4S)-4-tert-butyloxycarbonylmethyl-2-tert-butyl-5-oxo-1,3-dioxolan-4-yl)-3-butenoic acid

2-amino-3-(4-tert-butoxy-phenyl)-propionic acid tert-butyl ester

(2S,3S)-2-hydroxy-3-(hydroxycarbonyl)-4-pentenoic acid

(2S,3S)-2-hydroxy-3-(hydroxycarbonyl)-4-pentenoate

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