(3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one
• CAS No.: 183066-56-0
• Molecular Formula: C₂₅H₂₄N₂O₃
• Molecular Weight: 400.477

Synonyms:(3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one

Chemical Property of (3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one

Chemical Property:

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Technology Process of (3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one

There total 2 articles about (3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one 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: 95.0%

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone (148968-08-5) + benzylamine (100-46-9) → (3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one (183066-56-0)

Guidance literature:

With magnesium sulfate; In dichloromethane; Ambient temperature;

DOI:10.1021/jo960826c

Reference yield:

(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one (115857-84-6) → (3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one (183066-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) p-TsOH, 2.) NaIO₄ / 1.) THF, H₂O, reflux, 12 h, 2.) MeOH, H₂O, room temperature, 14 h

2: 95 percent / MgSO₄ / CH₂Cl₂ / Ambient temperature

With sodium periodate; magnesium sulfate; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1021/jo960826c

Reference yield: 85.0%

Benzyloxyacetyl chloride (19810-31-2) + (3R,4S)-4-[(E)-Benzylimino-methyl]-3-benzyloxy-1-(4-methoxy-phenyl)-azetidin-2-one (183066-56-0) → (2S,3R,2'S,3'R)-1'-Benzyl-3,3'-bis-benzyloxy-1-(4-methoxy-phenyl)-[2,2']biazetidinyl-4,4'-dione (183066-52-6)

Guidance literature:

With triethylamine; In toluene; for 3h; Ambient temperature;

DOI:10.1021/jo960826c

upstream raw materials:

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone

benzylamine

(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one

Downstream raw materials:

(2S,3R,2'S,3'R)-1'-Benzyl-3,3'-bis-benzyloxy-1-(4-methoxy-phenyl)-[2,2']biazetidinyl-4,4'-dione

Acetic acid (2S,3R,2'S,3'R)-1-benzyl-3'-benzyloxy-1'-(4-methoxy-phenyl)-4,4'-dioxo-[2,2']biazetidinyl-3-yl ester

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