(S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester

Base Information

• Chemical Name: (S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester
• CAS No.: 16305-90-1
• Molecular Formula: C₁₈H₂₄N₄O₇
• Molecular Weight: 408.411

Synonyms:(S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester

Chemical Property of (S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester

There total 1 articles about (S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric 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: 78.0%

L-glutamine methyl ester (40846-98-8,108258-30-6) + N-benzyloxycarbonyl-L-asparagine (2304-96-3) → (S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester (16305-90-1)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 10h;

DOI:10.1021/acs.orglett.8b02652

Reference yield:

(S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester (16305-90-1) → C63H79N5O11

Guidance literature:

Multi-step reaction with 6 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / Sealed tube

2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 10 h / 0 - 20 °C

3: lithium hydroxide monohydrate / methanol; water / 4 h / 0 - 20 °C

4: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 10 h / 0 - 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 20 °C

6: iron(II) chloride / ethanol / 3 h / 80 °C

With 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; iron(II) chloride; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; 6: |Wacker Oxidation;

DOI:10.1021/acs.orglett.8b02652

Reference yield:

(S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester (16305-90-1) → asperphenin A

Guidance literature:

Multi-step reaction with 7 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / Sealed tube

2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 10 h / 0 - 20 °C

3: lithium hydroxide monohydrate / methanol; water / 4 h / 0 - 20 °C

4: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 10 h / 0 - 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 20 °C

6: iron(II) chloride / ethanol / 3 h / 80 °C

7: 10% palladium hydroxide on charcoal; hydrogen / methanol; water / 3 h / 20 °C / Sealed tube

With 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; 10% palladium hydroxide on charcoal; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; iron(II) chloride; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; 6: |Wacker Oxidation;

DOI:10.1021/acs.orglett.8b02652

upstream raw materials:

L-glutamine methyl ester

N-benzyloxycarbonyl-L-asparagine

Downstream raw materials:

[(S)-2-Carbamoyl-1-((S)-3-carbamoyl-1-hydrazinocarbonyl-propylcarbamoyl)-ethyl]-carbamic acid benzyl ester

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