(S)-N-((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-2-[2-oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionamide

Base Information

• Chemical Name: (S)-N-((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-2-[2-oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionamide
• CAS No.: 195071-89-7
• Molecular Formula: C₂₈H₂₉N₃O₆
• Molecular Weight: 503.555
• Mol file: 195071-89-7.mol

Synonyms:

Chemical Property of (S)-N-((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-2-[2-oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-2-[2-oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionamide

There total 5 articles about (S)-N-((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-2-[2-oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionamide 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:

3-(benzyloxycarbonylamino)pyrid-2-one (147269-67-8) → (S)-N-((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-2-[2-oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionamide (195071-89-7)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran

2: H₂ / Pd/C / methanol

3: NaHCO₃ / dioxane

4: aq. NaOH / methanol

5: 1.) Bu₃SnH, (Ph₃P)2PdCl₂, 2.) HOBt, EDC / 1.) DMF, CH₂Cl₂, 5 min, 2.) 0 deg C to 20 deg C, 18 h

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1016/S0960-894X(97)00394-6

Reference yield:

methyl (2S)-2-(3-{[(benzyloxy)carbonyl]amino}-2-oxo-1,2-dihydropyridin-1-yl)propanoate (175210-52-3) → (S)-N-((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-2-[2-oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionamide (195071-89-7)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd/C / methanol

2: NaHCO₃ / dioxane

3: aq. NaOH / methanol

4: 1.) Bu₃SnH, (Ph₃P)2PdCl₂, 2.) HOBt, EDC / 1.) DMF, CH₂Cl₂, 5 min, 2.) 0 deg C to 20 deg C, 18 h

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; hydrogen; tri-n-butyl-tin hydride; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol;

DOI:10.1016/S0960-894X(97)00394-6

Reference yield:

(S)-2-(3-Amino-2-oxo-2H-pyridin-1-yl)-propionic acid methyl ester (175210-61-4) → (S)-N-((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-2-[2-oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionamide (195071-89-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NaHCO₃ / dioxane

2: aq. NaOH / methanol

3: 1.) Bu₃SnH, (Ph₃P)2PdCl₂, 2.) HOBt, EDC / 1.) DMF, CH₂Cl₂, 5 min, 2.) 0 deg C to 20 deg C, 18 h

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; methanol;

DOI:10.1016/S0960-894X(97)00394-6

upstream raw materials:

(2RS,3S)-3-allyloxycarbonylamino-2-benzyloxy-5-oxotetrahydrofuran

(S)-2-[2-Oxo-3-(3-phenyl-propionylamino)-2H-pyridin-1-yl]-propionic acid

3-(benzyloxycarbonylamino)pyrid-2-one

(S)-2-(3-Amino-2-oxo-2H-pyridin-1-yl)-propionic acid methyl ester