7-[3-tert-butoxycarbonyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid tert-butyl ester

Base Information

• Chemical Name: 7-[3-tert-butoxycarbonyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid tert-butyl ester
• CAS No.: 674787-30-5
• Molecular Formula: C₄₆H₆₁N₃O₉
• Molecular Weight: 800.005

Synonyms:

Chemical Property of 7-[3-tert-butoxycarbonyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[3-tert-butoxycarbonyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid tert-butyl ester

There total 7 articles about 7-[3-tert-butoxycarbonyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic 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:

phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate (143601-50-7) → 7-[3-tert-butoxycarbonyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid tert-butyl ester (674787-30-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.1: Rh(PPh₃)3; catechol borane / tetrahydrofuran / 1.5 h / 20 °C

2.2: 73 percent / aq. H₂O₂; KH₂PO₄ / tetrahydrofuran; ethanol / 12 h / 20 °C / pH 7.2

3.1: 76 percent / aq. NaIO₄; RuCl₃ / acetonitrile; CCl₄ / 2 h

4.1: 50 percent / H₂SO₄ / CH₂Cl₂; dioxane / 48 h

5.1: 2-hydroxypyridin / 72 h

6.1: H₂ / Pd/C / ethanol / 2 h

7.1: EDT; HOBt; NMM / dimethylformamide / 20 h

With 4-methyl-morpholine; 2-hydroxypyridin; ruthenium trichloride; sodium periodate; 3>; ethylenediaminetetraacetic acid; sulfuric acid; hydrogen; benzotriazol-1-ol; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Sharpless oxidation;

DOI:10.1016/j.bmcl.2003.11.061

Reference yield:

[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester (674787-19-0) → 7-[3-tert-butoxycarbonyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid tert-butyl ester (674787-30-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Rh(PPh₃)3; catechol borane / tetrahydrofuran / 1.5 h / 20 °C

1.2: 73 percent / aq. H₂O₂; KH₂PO₄ / tetrahydrofuran; ethanol / 12 h / 20 °C / pH 7.2

2.1: 76 percent / aq. NaIO₄; RuCl₃ / acetonitrile; CCl₄ / 2 h

3.1: 50 percent / H₂SO₄ / CH₂Cl₂; dioxane / 48 h

4.1: 2-hydroxypyridin / 72 h

5.1: H₂ / Pd/C / ethanol / 2 h

6.1: EDT; HOBt; NMM / dimethylformamide / 20 h

With 4-methyl-morpholine; 2-hydroxypyridin; ruthenium trichloride; sodium periodate; 3>; ethylenediaminetetraacetic acid; sulfuric acid; hydrogen; benzotriazol-1-ol; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Sharpless oxidation;

DOI:10.1016/j.bmcl.2003.11.061

Reference yield:

{(S)-1-[(2S,4R)-4-(3-Hydroxy-propyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid benzyl ester (674787-20-3) → 7-[3-tert-butoxycarbonyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid tert-butyl ester (674787-30-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / aq. NaIO₄; RuCl₃ / acetonitrile; CCl₄ / 2 h

2: 50 percent / H₂SO₄ / CH₂Cl₂; dioxane / 48 h

3: 2-hydroxypyridin / 72 h

4: H₂ / Pd/C / ethanol / 2 h

5: EDT; HOBt; NMM / dimethylformamide / 20 h

With 4-methyl-morpholine; 2-hydroxypyridin; ruthenium trichloride; sodium periodate; ethylenediaminetetraacetic acid; sulfuric acid; hydrogen; benzotriazol-1-ol; palladium on activated charcoal; In 1,4-dioxane; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Sharpless oxidation;

DOI:10.1016/j.bmcl.2003.11.061

upstream raw materials:

phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate

[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

{(S)-1-[(2S,4R)-4-(3-Hydroxy-propyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid benzyl ester

3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid

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