104227-75-0

Upstream product

• 50-00-0 formaldehyd 
• 92445-49-3 1-(isocyanomethyl)-4-nitrobenzene 

Downstream Products

• 128791-76-4 p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate 
• 128791-75-3 p-nitrobenzyl (2S,3S)-3-azido-2-(tert-butyldimethylsiloxymethyl)-4-oxoazetidine-1-acetate 
• 128791-73-1 p-nitrobenzyl (6S,7S)-3-methoxy-8-oxo-7-phenylacetamido-4-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 
• 128791-77-5 p-nitrobenzyl (2S,3S)-2-(imidazol-1-yl)carbonyloxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate 
• 192517-58-1 ((2S,3S)-3-Azido-2-hydroxymethyl-4-oxo-azetidin-1-yl)-acetic acid 4-nitro-benzyl ester 
• 192517-62-7 [(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 
• 128791-74-2 2-[(2S,3S)-3-Azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-azetidin-1-yl]-N-(4-nitro-benzyl)-acetamide 

Relevant academic research and scientific papers

Enantioselective synthesis of 2-isocephem and 2-isooxacephem antibiotics

The azido lactone 8 was prepared in a highly stereoselective manner by introduction of an azide function to the lactone 6 derived from L-aspartic acid, and then was converted into (2S,3S)-3-amino-2-azido-4-hydroxybutanoic acid 4. Four-component condensation of the amino acid 4, p-nitrobenzyl isocyanide and formaldehyde or 2,2-diethoxyacetaldehyde furnished the corresponding 3,4-cis-azetidinone 16 or 26 in excellent yield. 3-Methoxy-2-isooxacephalosporin was prepared by the intramolecular acylation of imidazolide 23 derived from compound 16. 3-Unsubstituted 2-isocephem and 2-isooxacephem analogues were prepared from the azetidinone 26.