150949-66-9

Upstream product

• 277331-22-3 (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-2-azetidinone 
• 1025887-95-9 Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine 
• 179949-34-9 (3R,4S)-4-((1S,2S)-1-Amino-2-hydroxy-2-phenyl-ethyl)-1-benzyl-3-benzyloxy-azetidin-2-one 
• 131319-74-9 (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine 
• 100-46-9 benzylamine 
• 139007-45-7 S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate 
• 153472-23-2 C₃₉H₄₀N₂O₆ 
• 153472-19-6 Benzyl-[1-{(4S,5S)-5-[(E)-benzylimino-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine 
• 179949-30-5 (3R,4S,4'S,5'S) N-benzyl-3-benzyloxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one 
• 213480-19-4 (3R,4S)-3-acetoxy-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]azetidin-2-one 
• 190007-78-4 (3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-hydroxyazetidin-2-one 
• 100-39-0 benzyl bromide 
• 260354-47-0 (3R,4S)-1-Benzyl-3-benzyloxy-4-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-azetidin-2-one 
• 143159-97-1 (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone 

Downstream Products

• 277331-35-8 (+)-(3R,4S)-1-benzyl-3-benzyloxy-4-formyl-2-azetidinone 
• 351340-19-7 (3R,4S)-1-Benzyl-3-benzyloxy-4-((E)-styryl)-azetidin-2-one 
• 351340-21-1 (3R,4S)-1-Benzyl-3-benzyloxy-4-[(E)-2-(4-methoxy-phenyl)-vinyl]-azetidin-2-one 
• 130115-20-7 (3R,4R,4'R)-4-<<<(1,1-Dimethylethyl)dimethylsilyl>oxy>phenylmethyl>-3-phenylmethoxy-1-(phenylmethyl)azetidin-2-one 
• 162780-09-8 (S)-3-Benzyl-4-[2-(4-methoxy-phenyl)-ethyl]-oxazolidine-2,5-dione 
• 162780-02-1 (S)-1-Benzyl-4-[2-(4-methoxy-phenyl)-ethyl]-azetidine-2,3-dione 
• 162780-24-7 (S)-3-Benzyl-4-(4-methoxy-benzyl)-oxazolidine-2,5-dione 
• 162780-10-1 (S)-3-Benzyl-4-(2-p-tolyl-ethyl)-oxazolidine-2,5-dione 
• 162779-95-5 (3R,4S)-1-Benzyl-3-hydroxy-4-[2-(4-methoxy-phenyl)-ethyl]-azetidin-2-one 

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.

A strategy for the asymmetric aminohomologation of α,β-dihydroxy aldehydes: Application to the synthesis of the southwest tripeptide segment of echinocandin B

The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic

Base-promoted isomerization of cis-4-formyl-2-azetidinones: Chemoselective C4-epimerization vs rearrangement to cyclic enaminones

Two simple, efficient, and complementary methods for the regiospecific C4-epimerization of cis-4-formyl-2-azetidinones 1-3 are described. The first method uses 40% aqueous dimethylamine as reagent in heterogeneous medium with benzene at room temperature, in the presence of benzyltributylammonium bromide (3-4 mol %) as the phase-transfer catalyst. This transformation tolerates alkyl, alkenyl, alkynyl, aryl, and alkoxy substituents at the C3 of the 2-azetidinone ring. However, limitations of this isomerization are as follows: (i) only N-(p-methoxyphenyl)-β-lactams can be used, and (ii) transformation is less compatible with heteroatomic substituents bonded to the C3 position of the 2-azetidinone ring. A highly general solution to these problems relies on the use of sodium carbonate as the isomerization reagent in different solvents. We also describe a novel base-promoted rearrangement of the β-lactam ring to cyclic enaminones 6 and 21, involving an E1cB-elimination reaction in cis-4-formyl-2-azetidinones.

Synthetic studies towards peptidyl nucleoside antibiotics: First synthesis of a polyoxamic acid derivative enabling direct coupling with α-amino acid esters

The reaction of the Mukaiyama's aldehyde-derived N-benzyl imine with an hydroxyketene equivalent followed by exposure of the resulting α-hydroxy β-lactam to NaOCl and 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO) provides a novel α-amino acid N-carboxy an

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