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

Base Information

• Chemical Name: (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid dibenzyl ester
• CAS No.: 148696-49-5
• Molecular Formula: C₂₉H₂₈N₂O₅
• Molecular Weight: 484.552
• Mol file: 148696-49-5.mol

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

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

There total 8 articles about (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid dibenzyl 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: 85.0%

(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-5-oxo-pentanoic acid benzyl ester (148696-51-9) → (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid dibenzyl ester (148696-49-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; Heating;

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

Reference yield: 80.0%

(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-5-methoxy-pyrrolidine-2-carboxylic acid benzyl ester → (2S,5S,7aR)-2-Benzyl-3-oxo-hexahydro-pyrrolo[1,2-a]imidazole-1,5-dicarboxylic acid dibenzyl ester (148696-49-5)

Guidance literature:

With boron trifluoride diethyl etherate;

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 dibenzyl ester (148696-49-5)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 85 percent / trifluoroacetic acid / CH₂Cl₂ / Heating

With 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

upstream raw materials:

(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-5-oxo-pentanoic acid benzyl 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

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