(+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone

Base Information

• Chemical Name: (+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone
• CAS No.: 164354-37-4
• Molecular Formula: C₂₃H₂₀N₂O₃
• Molecular Weight: 372.423

Synonyms:(+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone

Chemical Property of (+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone

Chemical Property:

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Technology Process of (+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone

There total 1 articles about (+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone 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:

(E)-3-phenylpropenal (14371-10-9) → (+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone (164354-37-4)

Guidance literature:

Multi-step reaction with 2 steps

1: MgSO₄ / CH₂Cl₂ / 20 °C

2: 2.86 g / Et₃N; PhOP(O)Cl₂ / CH₂Cl₂ / 0 - 20 °C

With magnesium sulfate; O-phenyl phosphorodichloridate; triethylamine; In dichloromethane; 1: Condensation / 2: Staudinger cyclization;

DOI:10.1021/jo9823994

Reference yield: 85.0%

toluene-p-sulfonyl bromide (1950-69-2) + (+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone (164354-37-4) → 1-(α-bromobenzyl)-2-(Z-p-toluenesulfonylmethylene)-6-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]carbapenam (244248-97-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; Heating;

DOI:10.1021/jo9823994

Reference yield: 75.0%

diphenylphosphane (829-85-6) + (+)-(3S,4R)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-1-propargyl-4-(E)-styryl-2-azetidinone (164354-37-4) → (4S,5R,6S)-4-Benzyl-3-[1-diphenylphosphanyl-meth-(Z)-ylidene]-6-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-1-aza-bicyclo[3.2.0]heptan-7-one (244248-96-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; Heating;

DOI:10.1021/jo9823994

upstream raw materials:

(E)-3-phenylpropenal

Downstream raw materials:

1-(α-bromobenzyl)-2-(Z-p-toluenesulfonylmethylene)-6-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]carbapenam

(4S,5R,6S)-4-Benzyl-3-[1-diphenylphosphanyl-meth-(Z)-ylidene]-6-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-1-aza-bicyclo[3.2.0]heptan-7-one

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