78738-80-4

Basic information

• Product Name: 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one
• Synonyms: 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one
• CAS NO: 78738-80-4
• Molecular Weight: 316.36
• Mol File: 78738-80-4.mol

Chemical Properties

• CAS DataBase Reference: 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one(78738-80-4)
• EPA Substance Registry System: 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one(78738-80-4)

Safety Data

• Hazardous Substances Data: 78738-80-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 21691-50-9 Ala-OtBu 
• 30426-58-5 2-azidoacetyl chloride 
• 78688-64-9 (S)-N-benzylidene-1-t-butoxycarbonylethylamine 

Downstream Products

• 136693-88-4 (2R,5S)-1-phenyl-2-amino-5-methyl-7-oxa-4-azaheptane 
• 78738-82-6 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-(benzylideneamino)-4-phenylazetidin-2-one 
• 78738-81-5 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-<(3'S,4'R)-3-azido-4-phenylazetidin-2-on-1-yl>-4-phenylazetidin-2-one 
• 78688-65-0 (S)-2-((3S,4R,3'R,4'S)-3-Acetylamino-2,2'-dioxo-4,4'-diphenyl-[1,3']biazetidinyl-1'-yl)-propionic acid tert-butyl ester 
• 107010-75-3 (S)-2-((3S,4R,3'R,4'S)-3-Amino-2,2'-dioxo-4,4'-diphenyl-[1,3']biazetidinyl-1'-yl)-propionic acid tert-butyl ester 
• 78688-68-3 (S)-2-((3R,4S)-2-Oxo-4-phenyl-3-{[1-phenyl-meth-(E)-ylidene]-amino}-azetidin-1-yl)-propionic acid tert-butyl ester 
• 83198-12-3 (S)-2-((3R,4S)-3-Amino-2-oxo-4-phenyl-azetidin-1-yl)-propionic acid tert-butyl ester 
• 136693-78-2 (2S,3S)-1-<(S)-2-hydroxy-1-methylethyl>-2-phenyl-3-aminoazetidine 

Relevant articles and documents

Effective Method for the Asymmetric Synthesis of Bis-β-lactams by the Cycloaddition of Azidoketen to Benzylideneamines Bearing a Chiral β-Lactam Backbone

Extremely high stereoselectivity was observed in the asymmetric cycloaddition of azidoketen to 1--3-benzylideneamino-4-phenylazetidin-2-ones, which gave rise to the formation of optically pure bis-β-lactams.

Remarkable Effects of Lone Pair-Lone Pair Interactions on the Extremely Stereoselective Cycloaddition of Azidoketene to Chiral 3-Imino-β-lactams

The stereoselective cycloaddition of azidoketene to cis-3-imino-β-lactams 1, 2, and 3, trans-3-imino-β-lactam 4, and cis-3-iminoazetidine 5 were carried out.It was found that the reactions of 1, 2, and 3 proceeded with > 99.5 percent stereoselectivity to give bis-β-lactams 9, 14, and 19, respectively.The reaction of 4 gave a bis-β-lactam 20 with 62 percent de, and the reaction of 5 gave a β-lactamazetidine 21 with 32 percent de including the asymmetry in the opposite direction.These results clearly indicate that, in addition to the conventional steric effects, the lone pair-lone pair interaction of β-lactam oxygen with the intermediate betaine's oxygen is the crucial factor for the extremely stereoselective cycloaddition of azidoketene to 1, 2, and 3.Possible mechanisms for these stereoselective cycloadditions are proposed.The X-ray crystal structure of 3a and the calculated energy-minimum conformations of 3a, 4, and 5 with MODEL-MM2-ROTOCHEM programs are provided.