2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl ester

Base Information

• Chemical Name: 2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl ester
• CAS No.: 264921-67-7
• Molecular Formula: C₅₁H₈₀N₄O₁₀Si
• Molecular Weight: 937.302

Synonyms:2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl ester

Chemical Property of 2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl ester

There total 18 articles about 2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl 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:

1,4-pentadienyl-3-diazoacetate (156418-79-0) → 2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl ester (264921-67-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Rh₂[(5S)-MEPY]4 / CH₂Cl₂ / Heating

2.1: O₃ / methanol; CH₂Cl₂ / -78 °C

2.2: 60 percent / NaBH₄ / methanol; CH₂Cl₂ / 0.5 h / -78 - 0 °C

3.1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 0.15 g / NaN₃ / dimethylformamide / 12 h / 65 °C

5.1: conc. HCl / 12 h / 20 °C

6.1: 0.33 g / imidazole / dimethylformamide / 12 h / 20 °C

7.1: H₂ / Pd/C / methanol / 1 h / 760.05 Torr

8.1: 0.18 g / EDCI; HOBt / dimethylformamide / 16 h / 0 - 20 °C

9.1: 90 percent / aq. NaOH / ethanol / 14 h / 0 - 20 °C

10.1: DCC / CH₂Cl₂ / 1 h / 20 °C

11.1: 46 mg / Pd(PPh₃)4; Bu₃SnH / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; hydrogen; tri-n-butyl-tin hydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Cyclization / 2.1: ozonolysis / 2.2: Reduction / 3.1: Condensation / 4.1: Substitution / 5.1: Esterification / 6.1: Condensation / 7.1: Reduction / 8.1: Condensation / 9.1: Hydrolysis / 10.1: Esterification / 11.1: Condensation;

DOI:10.1021/jo991288h

Reference yield:

[1S-(1α,4α,5α)]-4-vinyl-3-oxabicyclo[3.1.0]hexan-2-one (156418-83-6) → 2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl ester (264921-67-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: O₃ / methanol; CH₂Cl₂ / -78 °C

1.2: 60 percent / NaBH₄ / methanol; CH₂Cl₂ / 0.5 h / -78 - 0 °C

2.1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

3.1: 0.15 g / NaN₃ / dimethylformamide / 12 h / 65 °C

4.1: conc. HCl / 12 h / 20 °C

5.1: 0.33 g / imidazole / dimethylformamide / 12 h / 20 °C

6.1: H₂ / Pd/C / methanol / 1 h / 760.05 Torr

7.1: 0.18 g / EDCI; HOBt / dimethylformamide / 16 h / 0 - 20 °C

8.1: 90 percent / aq. NaOH / ethanol / 14 h / 0 - 20 °C

9.1: DCC / CH₂Cl₂ / 1 h / 20 °C

10.1: 46 mg / Pd(PPh₃)4; Bu₃SnH / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; hydrogen; tri-n-butyl-tin hydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: ozonolysis / 1.2: Reduction / 2.1: Condensation / 3.1: Substitution / 4.1: Esterification / 5.1: Condensation / 6.1: Reduction / 7.1: Condensation / 8.1: Hydrolysis / 9.1: Esterification / 10.1: Condensation;

DOI:10.1021/jo991288h

Reference yield:

[1S-(1α,4α,5α)]-4-hydroxymethyl-3-oxabicyclo[3.1.0]hexan-2-one (264921-37-1) → 2-{tert-butoxycarbonyl-[2-({2-[2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarbonyl}-amino)-3-phenyl-cyclopropyl]-amino}-4-methyl-pentanoic acid methyl ester (264921-67-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 0.15 g / NaN₃ / dimethylformamide / 12 h / 65 °C

3: conc. HCl / 12 h / 20 °C

4: 0.33 g / imidazole / dimethylformamide / 12 h / 20 °C

5: H₂ / Pd/C / methanol / 1 h / 760.05 Torr

6: 0.18 g / EDCI; HOBt / dimethylformamide / 16 h / 0 - 20 °C

7: 90 percent / aq. NaOH / ethanol / 14 h / 0 - 20 °C

8: DCC / CH₂Cl₂ / 1 h / 20 °C

9: 46 mg / Pd(PPh₃)4; Bu₃SnH / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; hydrogen; tri-n-butyl-tin hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Substitution / 3: Esterification / 4: Condensation / 5: Reduction / 6: Condensation / 7: Hydrolysis / 8: Esterification / 9: Condensation;

DOI:10.1021/jo991288h

upstream raw materials:

[1S-(1α,2α,3β)]-2-[(allyloxycarbonyl)amino]-1-[N-(tert-butoxycarbonyl)-L-leucine methyl ester]-2-carboxy-3-phenylcyclopropane

di-tert-butyl dicarbonate

1,4-pentadienyl-3-diazoacetate

[1S-(1α,4α,5α)]-4-vinyl-3-oxabicyclo[3.1.0]hexan-2-one

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