145654-57-5

Basic information

• Product Name: (3S,4R)-3-Benzyloxy-4-(4-methoxy-phenyl)-azetidin-2-one
• CAS NO: 145654-57-5
• Molecular Weight: 283.327
• Mol File: 145654-57-5.mol

Chemical Properties

• CAS DataBase Reference: (3S,4R)-3-Benzyloxy-4-(4-methoxy-phenyl)-azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-3-Benzyloxy-4-(4-methoxy-phenyl)-azetidin-2-one(145654-57-5)
• EPA Substance Registry System: (3S,4R)-3-Benzyloxy-4-(4-methoxy-phenyl)-azetidin-2-one(145654-57-5)

Safety Data

• Hazardous Substances Data: 145654-57-5(Hazardous Substances Data)

Upstream product

• 145654-49-5 cis-4-p-Anisyl-1-<(4'-methoxybenzylidene)amino>-3-benzyloxy-2-azetidinone 
• 19810-31-2 Benzyloxyacetyl chloride 
• 132127-28-7 N-trimethylsilyl-(4-methoxybenzaldimine) 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 145654-53-1 1-((Z)-2-Benzyloxy-vinyl)-4-methoxy-benzene 

Relevant articles and documents

Highly syn-diastereoselective synthesis of NH-3-benzyloxy-4-aryl-azetidin-2-ones via a two-step Staudinger reaction

New conditions for the Staudinger reaction provide NH-3-benzyloxy-4-aryl-β-lactams in good yields with complete cis-diastereoselectivity.

2,3-Diaza-1,3-dienes (azines) as substrates for the Staudinger reaction. Synthesis and reactivity of N-imino-β-lactams

The reaction of aromatic and aliphatic azines with different ketene precursors, such as the acid chloride/Et3N system, alkoxychromium(0) carbenes, and free diphenyl ketene, gives N-imino-β-lactams in good to excellent yields, with good levels of cis,trans-selectivity. A wide variety of symmetrically-substituted azines derived from aldehydes and ketones are compatible with the Staudinger reaction. Chiral N-imino-β-lactams derived from symmetrically or unsymmetrically (mixed) chiral azines are also obtained in good yields as essentially single enantiomers (de > 95%). Different reaction intermediates, including hemiaminals, oxadiazols, and hydrazides have been isolated. Free diphenyl ketene forms Diels-Alder adducts and N-acylazadienes in addition to the previously reported N-imino-β-lactams. The usual reactivity of the β-lactam ring is modified in N-imino-β-lactams by the presence of the imino group. Thus, β-hydrazonoesters, N-alkylamino-β-lactams, and NH-β-lactams can be efficiently obtained by base-catalyzed 2-azetidinone ring opening, catalytic hydrogenation, and ozonolysis, respectively.