153472-33-4

Upstream product

• 100-46-9 benzylamine 
• 131319-74-9 (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine 
• 153472-19-6 Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine 
• 701-99-5 Phenoxyacetyl chloride 
• 179949-33-8 (3R,4S)-4-((1S,2S)-1-Amino-2-hydroxy-2-phenyl-ethyl)-1-benzyl-3-phenoxy-azetidin-2-one 
• 153472-29-8 (1S,2S,3'R,4'S)-1,2-Bis(1'-benzyl-2'-oxo-3'-phenoxyazetidin-4'-yl)ethane-1,2-diol 
• 153472-22-1 (4S,5S,3'R,4'S)-2,2-Dimethyl-4,5-bis(1'-benzyl-2'-oxo-3'-phenoxyazetidin-4'-yl)-1,3-dioxolane 
• 148903-80-4 (3R,4S,4'S,5'S) N-benzyl-3-phenoxy-4-azetidin-2-one 

Downstream Products

• 690269-42-2 (3R,4S)-1-Benzyl-4-(1-hydroxy-2-nitro-ethyl)-3-phenoxy-azetidin-2-one 
• 632356-84-4 (3R,4S)-1-benzyl-4-(2-nitrovinyl)-3-phenoxyazetidin-2-one 
• 632356-92-4 (3R,4S)-1-benzyl-4-(2-nitroethyl)-3-phenoxyazetidin-2-one 
• 632356-99-1 methyl (2R,3S)-3-(benzylamino)-5-nitro-2-phenoxypentanoate 
• 1399842-85-3 C₂₆H₂₃NO₃ 
• 1399843-02-7 C₂₆H₂₁NO₂ 
• 1418022-84-0 C₂₁H₂₁NO₃ 

Relevant academic research and scientific papers

Optically active 4-formyl β-lactams: Microwave-induced deacetonation-oxidation

Microwave-induced chiral synthesis of 4-formyl β-lactams is performed following a one-pot reaction. The deprotection of the ketal with aqueous bismuth nitrate and subsequent oxidation of the diol to aldehyde by aqueous sodium metaperiodate is accomplished

Asymmetric synthesis of 3,4-disubstituted 2-(trifluoromethyl)pyrrolidines through rearrangement of chiral 2-(2,2,2-trifluoro-1-hydroxyethyl)azetidines

Enantiopure 4-formyl-β-lactams were deployed as synthons for the diastereoselective formation of chiral 2-(2,2,2-trifluoro-1-hydroxyethyl)azetidines via trifluoromethylation through aldehyde modification followed by reductive removal of the β-lactam carbonyl moiety. Subsequent treatment of the (in situ) activated 2-trifluoroethylated azetidines with a variety of nitrogen, oxygen, sulfur, and fluorine nucleophiles afforded chiral 3,4-disubstituted 2-(trifluoromethyl)pyrrolidines in good to excellent yields (45-99%) and high diastereoselectivities (dr >99/1, 1H NMR) via interception of bicyclic aziridinium intermediates. Furthermore, representative pyrrolidines were N,O-debenzylated in a selective way and used for further synthetic elaboration to produce, for example, a CF3-substituted 2-oxa-4,7-diazabicyclo[3.3.0]octan-3-one system.

Application of (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol in the formal total synthesis of carbapenems, novel 4-cyano-β-lactams and β-hydroxy aspartates

The imines derived from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol furnished cis-β-lactams stereoselectively on the Staudinger reaction. These homochiral cis-β-lactams were converted in to cis-β-lactams possessing aminol side chain at C-4. These aminols