(2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl ester

Base Information

• Chemical Name: (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl ester
• CAS No.: 148696-56-4
• Molecular Formula: C₂₂H₂₂N₂O₅
• Molecular Weight: 394.427
• Mol file: 148696-56-4.mol

Synonyms:(2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl ester

Chemical Property of (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl ester

There total 8 articles about (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl 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: 81.0%

(2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid dibenzyl ester (148696-49-5) → (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl ester (148696-56-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran;

DOI:10.1016/0040-4039(93)85036-V

Reference yield:

N-Cbz-L-Phe (1161-13-3) → (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl ester (148696-56-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / i-BuOCOCl, Et₃N / tetrahydrofuran / 0 °C

2: 83 percent / OsO₄, NaIO₄ / dioxane; H₂O

3: 85 percent / trifluoroacetic acid / CH₂Cl₂ / Heating

4: 81 percent / aq. LiOH / tetrahydrofuran

With lithium hydroxide; sodium periodate; osmium(VIII) oxide; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1016/0040-4039(93)85036-V

Reference yield:

(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-hex-5-enoic acid benzyl ester (148696-50-8) → (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid 1-benzyl ester (148696-56-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / OsO₄, NaIO₄ / dioxane; H₂O

2: 85 percent / trifluoroacetic acid / CH₂Cl₂ / Heating

3: 81 percent / aq. LiOH / tetrahydrofuran

With lithium hydroxide; sodium periodate; osmium(VIII) oxide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1016/0040-4039(93)85036-V

upstream raw materials:

(2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid dibenzyl ester

N-Cbz-L-Phe

phenylmethyl (S)-2-amino-5-hexenoate

(2S)-2-amino-5-hexenoic acid

Downstream raw materials:

(2S,5S,7aR)-2-Benzyl-5-isobutylcarbamoyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1-carboxylic acid benzyl ester