2-[(2S,3S)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(2S,3S)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione
• CAS No.: 121534-28-9
• Molecular Formula: C₂₂H₂₀N₂O₄
• Molecular Weight: 376.412

Synonyms:2-[(2S,3S)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione

Chemical Property of 2-[(2S,3S)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

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Technology Process of 2-[(2S,3S)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione

There total 10 articles about 2-[(2S,3S)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione 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: 84.0%

N-phthaloylglycine chloride (6780-38-7) + Benzyl-[1-((R)-3,3-dimethyl-oxiranyl)-meth-(E)-ylidene]-amine (121534-22-3) → 2-[(2R,3R)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione (121534-28-9,126455-42-3) + 2-[(2S,3S)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione (121534-28-9)

Guidance literature:

With triethylamine; In dichloromethane; Yields of byproduct given; addition of triethylamine at -78 deg C, 0 deg C 3-5 h;

DOI:10.1016/S0040-4039(00)80680-2

Reference yield: 84.0%

N-phthaloylglycine chloride (6780-38-7) + Benzyl-[1-((R)-3,3-dimethyl-oxiranyl)-meth-(E)-ylidene]-amine (121534-22-3) → 2-[(2R,3R)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione (121534-28-9,126455-42-3) + 2-[(2S,3S)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione (121534-28-9)

Guidance literature:

With triethylamine; In dichloromethane; Yields of byproduct given; addition of triethylamine at -78 deg C, 0 deg C 3-5 h;

DOI:10.1016/S0040-4039(00)80680-2

Reference yield:

3-methyl-2-buten-1-ol (556-82-1) → 2-[(2R,3R)-1-Benzyl-2-((R)-3,3-dimethyl-oxiranyl)-4-oxo-azetidin-3-yl]-isoindole-1,3-dione (121534-28-9,126455-42-3)

Guidance literature:

Multi-step reaction with 4 steps

1: tert-butyl hydroperoxide, titanium isopropoxide / (-)-diisopropyl tartarate

3: 4 Angstroem molecular sieves / CH₂Cl₂ / 12 h / 25 °C

4: triethylamine / CH₂Cl₂ / addition of triethylamine at -78 deg C, 0 deg C 3-5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; triethylamine; (-)-diisopropyl tartrate; In dichloromethane;

DOI:10.1016/S0040-4039(00)80680-2

upstream raw materials:

N-phthaloylglycine chloride

Benzyl-[1-((R)-3,3-dimethyl-oxiranyl)-meth-(E)-ylidene]-amine

[(2R)-3,3-dimethyloxiran-2-yl]methanol

(S)-3,3-dimethyloxirane-2-carboxaldehyde

Downstream raw materials:

(2S,3S)-1-Benzyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidine-2-carbaldehyde

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